Patent US4178286A successfully refreshed from Google Patents.
US4178286A
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β-Lactams, their production, intermediates thereto and derivatives thereof
Assignee: Research Corp
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Filing: 1976-10-28
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Granted: 1979-12-11
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Expires: 1996-10-28
Abstract
Abstract γ-lactones are converted into both known and new azetidine carboxylic acids which can be transformed readily to the corresponding β-lactams by oxidative decarboxylation. The β-lactams and substitution products thereof are useful intermediates in the synthesis of biologically active lactams such as nocardicin.
Inventors
- 👤 Harry H. Wasserman
- 👤 Bruce H. Lipshutz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:04
CPC Classifications
C; C07; C07D; C07D201/00; C07D201/02; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07D205/095
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
188 words
A process for preparing a lactam from an aminocarboxylic acid of the formula ##STR28## where R 1 is selected from the group consisting of: (a) an alkenyl group of the formula ##STR29## wherein R 4 is phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl group or phenylalkenyl of 2-4 carbon atoms in the alkenyl group, each of which is unsubstituted or monosubstituted by lower alkyl, lower alkoxy or halogen; and R 5 , R 6 and R 7 are hydrogen or alkyl of 1-3 carbon atoms; and (b) an acetal of the formula ##STR30## wherein R 4 and R 5 have the above-indicated values while R 8 and R 9 are each alkyl of 1-6 carbon atoms or together form ethylenedioxy or propylenedioxy; which comprises oxygenation of a dianion formed at low temperatures by reacting said aminocarboxylic acid with a non-nucleophilic base whose corresponding conjugate acid has a pKa equal to or greater than 19 in a polar, aprotic solvent to form a corresponding dianion intermediate and acidification of said intermediate to form a corresponding lactam of the formula ##STR31## wherein R 1 has the above-indicated values.
Claim 2
Dependent Claim
188 words
A process for preparing a lactam from an aminocarboxylic acid of the formula ##STR28## where R 1 is selected from the group consisting of: (a) an alkenyl group of the formula ##STR29## wherein R 4 is phenyl, phenylalkyl of 1-4 carbon atoms in the alkyl group or phenylalkenyl of 2-4 carbon atoms in the alkenyl group, each of which is unsubstituted or monosubstituted by lower alkyl, lower alkoxy or halogen; and R 5 , R 6 and R 7 are hydrogen or alkyl of 1-3 carbon atoms; and (b) an acetal of the formula ##STR30## wherein R 4 and R 5 have the above-indicated values while R 8 and R 9 are each alkyl of 1-6 carbon atoms or together form ethylenedioxy or propylenedioxy; which comprises oxygenation of a dianion formed at low temperatures by reacting said aminocarboxylic acid with a non-nucleophilic base whose corresponding conjugate acid has a pKa equal to or greater than 19 in a polar, aprotic solvent to form a corresponding dianion intermediate and acidification of said intermediate to form a corresponding lactam of the formula ##STR31## wherein R 1 has the above-indicated values.
Claim 3
Dependent Claim
13 words
A process according to claim 1, wherein R 1 is said alkenyl group.
Claim 4
Dependent Claim
18 words
A process according to claim 2, wherein R 5 , R 6 and R 7 are each hydrogen.
Claim 5
Dependent Claim
13 words
A process according to claim 3, where R 4 is p-alkoxyphenyl or p-benzyloxyphenyl.
Claim 6
Dependent Claim
13 words
A process according to claim 1, wherein R 1 is an acetal group.
Claim 7
Dependent Claim
13 words
A process according to claim 5, wherein R 4 is p-alkoxyphenyl or p-benzyloxyphenyl.
Claim 8
Dependent Claim
34 words
A process according to claim 1, wherein said oxidative decarboxylation includes acidifying a dilithium salt of a hydroperoxy acid of the formula: ##STR32## wherein R 1 has the above-indicated values to form said lactam.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-10 | 1983-06-11 | 1983-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-10 | 1987-06-11 | 1987-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-10 | 1991-06-11 | 1991-12-11 | $7700.00 | Window Closed / Lapsed |