US4465626A
Expired / Lapsed
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Process for preparation, isolation and purification of dipeptide sweeteners
Assignee: Danisco Finland Oy
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Filing: 1982-12-13
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Granted: 1984-08-14
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Expires: 2002-12-13
Abstract
Abstract Aromatic sulfonic acid salts of certain dipeptide sweeteners which are L-aspartyl-D-alaninamides or L-aspartyl-D-serinamides, each substituted on amide nitrogen with an organic radical having a highly branched carbon skeleton; the process for preparing said salts by crystallization; and utilization of this crystallization process in processes for the preparation, isolation and purification of said amides.
Inventors
- 👤 Constantine Sklavounos
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:29
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06104; C07K5/06113; Y; Y10; Y10S; Y10S530/00; Y10S530/801
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
107 words
A process for the preparation of an L-aspartyl-D-amino acid dipeptide amide of the formula ##STR12## wherein A is hydrogen or hydroxy and X is S, SO or SO 2 , in the form of an acid addition salt with an aromatic sulfonic acid of the formula ##STR13## wherein R 1 is hydrogen, methyl or chloro and R 2 is hydrogen or methyl; which comprises (a) reacting an acid addition salt of L-aspartic acid anhydride of the formula ##STR14## with a D-amino acid amide of the formula ##STR15## wherein A and X are as previously defined; and (b) crystallizing the resulting L-aspartyl-D-amino acid dipeptide with said sulfonic acid.
Claim 2
Dependent Claim
107 words
A process for the preparation of an L-aspartyl-D-amino acid dipeptide amide of the formula ##STR12## wherein A is hydrogen or hydroxy and X is S, SO or SO 2 , in the form of an acid addition salt with an aromatic sulfonic acid of the formula ##STR13## wherein R 1 is hydrogen, methyl or chloro and R 2 is hydrogen or methyl; which comprises (a) reacting an acid addition salt of L-aspartic acid anhydride of the formula ##STR14## with a D-amino acid amide of the formula ##STR15## wherein A and X are as previously defined; and (b) crystallizing the resulting L-aspartyl-D-amino acid dipeptide with said sulfonic acid.
Claim 3
Dependent Claim
18 words
A process of claim 1 wherein the acid addition salt of the L-aspartic anhydride is the hydrochloride salt.
Claim 4
Dependent Claim
11 words
A process of claim 2 wherein X is SO 2 .
Claim 5
Dependent Claim
17 words
A process of claim 3 wherein A is hydrogen and the aromatic sulfonic acid is p-toluenesulfonic acid.
Claim 6
Dependent Claim
9 words
A process of claim 2 wherein X is SO.
Claim 7
Dependent Claim
9 words
A process of claim 2 wherein X is S.
Claim 8
Dependent Claim
9 words
A process of claim 6 wherein A is hydrogen.
Claim 9
Dependent Claim
13 words
The process of claim 7 wherein the aromatic sulfonic acid is p-toluenesulfonic acid.
Claim 10
Dependent Claim
14 words
The process of claim 7 wherein the aromatic sulfonic acid is beta-naphthalene sulfonic acid.
Claim 11
Dependent Claim
14 words
The process of claim 7 wherein the aromatic sulfonic acid is alpha-naphthalene sulfonic acid.
Claim 12
Dependent Claim
13 words
The process of claim 7 wherein the aromatic sulfonic acid is benzenesulfonic acid.
Claim 13
Dependent Claim
9 words
A process of claim 6 wherein A is hydroxy.
Claim 14
Dependent Claim
13 words
The process of claim 12 wherein the aromatic sulfonic acid is p-toluenesulfonic acid.
Claim 15
Dependent Claim
15 words
A process for the preparation of an L-aspartyl-D-amino acid dipeptide amide of the formula ##STR16##
Claim 16
Dependent Claim
15 words
A process for the preparation of an L-aspartyl-D-amino acid dipeptide amide of the formula ##STR16##
Claim 17
Dependent Claim
96 words
wherein A is hydrogen or hydroxy and X is S, SO or SO 2 , in the form of an acid addition salt with an aromatic sulfonic acid of the formula ##STR17## wherein R 1 is hydrogen, methyl or chloro and R 2 is hydrogen or methyl; which comprises (a) reacting L-aspartyl N-thiocarboxy anhydride of the formula ##STR18## with a D-amino acid amide of the formula ##STR19## wherein A and X are as previously defined; in an aqueous solvent at a basic pH; and (b) crystallizing the resulting L-aspartyl-D-amino acid dipeptide with said aromatic sulfonic acid.
Claim 18
Dependent Claim
96 words
wherein A is hydrogen or hydroxy and X is S, SO or SO 2 , in the form of an acid addition salt with an aromatic sulfonic acid of the formula ##STR17## wherein R 1 is hydrogen, methyl or chloro and R 2 is hydrogen or methyl; which comprises (a) reacting L-aspartyl N-thiocarboxy anhydride of the formula ##STR18## with a D-amino acid amide of the formula ##STR19## wherein A and X are as previously defined; in an aqueous solvent at a basic pH; and (b) crystallizing the resulting L-aspartyl-D-amino acid dipeptide with said aromatic sulfonic acid.
Claim 19
Dependent Claim
11 words
A process of claim 14 wherein X is SO 2 .
Claim 20
Dependent Claim
17 words
A process of claim 15 wherein A is hydrogen and the aromatic sulfonic acid is p-toluenesulfonic acid.
Claim 21
Dependent Claim
9 words
A process of claim 14 wherein X is SO.
Claim 22
Dependent Claim
9 words
A process of claim 14 wherein X is S.
Claim 23
Dependent Claim
9 words
A process of claim 18 wherein A is hydrogen.
Claim 24
Dependent Claim
13 words
The process of claim 19 wherein the aromatic sulfonic acid is p-toluenesulfonic acid.
Claim 25
Dependent Claim
14 words
The process of claim 19 wherein the aromatic sulfonic acid is beta-naphthalene sulfonic acid.
Claim 26
Dependent Claim
14 words
The process of claim 19 wherein the aromatic sulfonic acid is alpha-naphthalene sulfonic acid.
Claim 27
Dependent Claim
13 words
The process of claim 19 wherein the aromatic sulfonic acid is benzenesulfonic acid.
Claim 28
Dependent Claim
9 words
A process of claim 18 wherein A is hydroxy.
Claim 29
Dependent Claim
13 words
The process of claim 24 wherein the aromatic sulfonic acid is p-toluenesulfonic acid.
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) | 1987-08-14 | 1988-02-13 | 1988-08-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-14 | 1992-02-13 | 1992-08-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-14 | 1996-02-13 | 1996-08-14 | $7700.00 | Window Closed / Lapsed |