Patent US4016205A successfully refreshed from Google Patents.
US4016205A
Expired / Lapsed
US
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Process for the optical resolution of DL-2-(4-hydroxyphenyl)glycine
Assignee: Astellas Pharma Inc
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Filing: 1975-09-12
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Granted: 1977-04-05
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Expires: 1995-09-12
Abstract
Abstract This invention relates to a process of resolving D and L-2-(4-hydroxyphenyl) glycine. DL-2-(4-hydroxyphenyl) glycine is treated with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-Hydroxyphenyl) glycine. This mixture is treated with a solvent selected from the group consisting of isobutyl alcohol, a mixture of a lower alkanol and chloroform, or a mixture of a lower alkanol and toluene. The precipitate containing the d-3-bromo-2-oxo-10 bornanesulfonic acid salt of L-2-(4-hydroxyphenyl) glycine is collected. The corresponding acid salt of D-2-(hydroxyphenyl) glycine is collected from the mother liquor. D- and L-2-(4-hydroxyphenyl) glycine are then recovered by conventional means.
Inventors
- 👤 Kazuo Kariyone
- 👤 Hideo Yagi
- 👤 Kazuhiko Yoshida
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 17:00
CPC Classifications
C; C07; C07B; C07B57/00
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
70 words
A process for the resolution of D-and L-2-(4-hydroxyphenyl)glycine which comprises treating DL-2-(4-hydroxyphenyl)glycine with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-hyroxyphenyl)glycine, treating the mixture with a solvent selected from the group consisting of a mixture of lower alkanol and chloroform or a mixture of lower alkanol and toluene to selectively precipitate a solvate of the d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine with chloroform or toluene.
Claim 2
Dependent Claim
70 words
A process for the resolution of D-and L-2-(4-hydroxyphenyl)glycine which comprises treating DL-2-(4-hydroxyphenyl)glycine with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-hyroxyphenyl)glycine, treating the mixture with a solvent selected from the group consisting of a mixture of lower alkanol and chloroform or a mixture of lower alkanol and toluene to selectively precipitate a solvate of the d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine with chloroform or toluene.
Claim 3
Dependent Claim
11 words
The process according to claim 1 further comprising collecting said precipitate.
Claim 4
Dependent Claim
22 words
The process according to claim 2 further comprising obtained d-3-bromo-2-oxo-10-bornanesulfonic acid salt of D-2-(4-hydroxyphenyl) glycine from the mother liquor containing lower alkanol.
Claim 5
Dependent Claim
10 words
The process according to claim 3 wherein D-2-(4-hydroxyphenyl)glycine is isolated.
Claim 6
Dependent Claim
18 words
The process according to claim 1 wherein a mixture of chloroform and ethanol is used as said solvent.
Claim 7
Dependent Claim
19 words
The process according to claim 1 wherein a mixture of toluene and isopropyl alcohol is used as said solvent.
Claim 8
Dependent Claim
18 words
The process according to claim 4 wherein a mixture of chloroform and ethanol is used as said solvent.
Claim 9
Dependent Claim
19 words
The process according to claim 4 wherein a mixture of toluene and isopropyl alcohol is used as said solvent.
Claim 10
Dependent Claim
10 words
The process according to claim 1 wherein L-2-(4-hydroxyphenyl)glycine is isolated.
Claim 11
Dependent Claim
18 words
The process according to claim 9 wherein a mixture of chloroform and ethanol is used as said solvent.
Claim 12
Dependent Claim
19 words
The process according to claim 9 wherein a mixture of toluene and isopropyl alcohol is used as said solvent.
Claim 13
Dependent Claim
70 words
The process according to claim 3 wherein said D-2-(4-hyroxyphenyl)glycine is recovered from d-3-bromo-2-oxo-10-bornanesulfonic acid salt of D-2-(4-hydroxyphenyl)glycine by the method comprising: a. dissolving said salt in a polar solvent, b. treating said salt in said polar solvent with a base having a stronger basicity than DL-2-(4-hydroxyphenyl)glycine whereby a solution is formed, and c. adding acid to said solution to attain a pH value of about 5 whereby D-2-(4-hydroxyphenyl)glycine is precipitated.
Claim 14
Dependent Claim
16 words
The process according to claim 12 further comprising treating said precipitate to obtain substantially pure D-2-(4-hydroxyphenyl)glycine.
Claim 15
Dependent Claim
67 words
The process according to claim 1 wherein said L-2-(4-hydroxyphenyl)glycine is recovered from said solvate by the method comprising: a. dissolving said solvate in a polar solvent, b. treating said solvate in said polar solvent with a base having a stronger basicity than DL-2-(4-hydroxyphenyl)glycine whereby a solution is formed, and c. adding acid to said solution to attain a pH value of about 5 whereby L-2-(4-hydroxyphenyl)glycine is precipitated.
Claim 16
Dependent Claim
16 words
The process according to claim 14 further comprising treating said precipitate to obtain substantially pure L-2-(4-hydroxyphenyl)glycine.
Claim 17
Dependent Claim
54 words
A process for the resolution of D- and L-2-(4-hydroxyphenyl)glycine with comprises treating DL-2-(4-hydroxyphenyl)glycine with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-hydroxyphenyl) glycine, treating the mixture with an excess of isobutyl alcohol to selectively precipitate a solvate of the d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl) glycine with isobutyl alcohol.
Claim 18
Dependent Claim
54 words
A process for the resolution of D- and L-2-(4-hydroxyphenyl)glycine with comprises treating DL-2-(4-hydroxyphenyl)glycine with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-hydroxyphenyl) glycine, treating the mixture with an excess of isobutyl alcohol to selectively precipitate a solvate of the d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl) glycine with isobutyl alcohol.
Claim 19
Dependent Claim
11 words
The process according to claim 16 further comprising collecting said precipitate.
Claim 20
Dependent Claim
21 words
The process according to claim 17 further comprising obtaining d-3-2-oxo-10-bornanesulfonic acid salt of D-2-(4-hydroxyphenyl)glycine from the mother liquor containing isobutyl alcohol.
Claim 21
Dependent Claim
10 words
The process according to claim 18 wherein D-2-(4-hydroxyphenyl)glycine is isolated.
Claim 22
Dependent Claim
10 words
The process according to claim 17 wherein L-2-(4-hydroxyphenyl)glycine is isolated.
Claim 23
Dependent Claim
70 words
The process according to claim 18 wherein said D-2-(4-hydroxyphenyl)glycine is recovered from d-3-bromo-2-oxo-10-bornanesulfonic acid salt of D-2-(4-hydroxyphenyl)glycine by the method comprising: a. dissolving said salt in a polar solvent, b. treating said salt in said polar solvent with a base having a stronger basicity than DL-2-(4-hydroxyphenyl)glycine whereby a solution is formed, and c. adding acid to said solution to attain a pH value of about 5 whereby D-2-(4-hydroxyphenyl)glycine is precipitated.
Claim 24
Dependent Claim
16 words
The process according to claim 21 further comprising treating said precipitate to obtain substantially pure D-2-(4-hydroxyphenyl)glycine.
Claim 25
Dependent Claim
67 words
The process according to claim 12 wherein said L-2-(4-hydroxyphenyl)glycine is recovered from said solvate by the method comprising: a. dissolving said solvate in a polar solvent, b. treating said solvate in said polar solvent with a base having a stronger basicity than DL-2-(4-hydroxyphenyl)glycine whereby a solution is formed, and c. adding acid to said solution to attain a pH value of about 5 whereby L-2-(4-hydroxyphenyl)glycine is precipitated.
Claim 26
Dependent Claim
16 words
The process according to claim 23 further comprising treating said precipitate to obtain substantially pure L-2-(4-hydroxyphenyl)glycine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-04 | 1980-10-04 | 1981-04-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-04 | 1984-10-04 | 1985-04-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-04 | 1988-10-04 | 1989-04-05 | $7700.00 | Window Closed / Lapsed |