Claims
- 1. The process for preparing a substituted .beta.-lactam compound of the formula ##STR23## which comprises a) reacting in an inert, anhydrous solvent at a temperature between -90.degree. and -15.degree. C. a .beta.-lactam ester of the formula ##STR24## with between 2 and 6 equivalents per 1 equivalent of .beta.-lactam ester of an alkali metal salt of the formula
- M.sup.+- 0-R.sub.2.
- in the presence of an excess of the corresponding alcohol of the formula HOR.sub. 2 ; b) adding between 1 and 5 equivalents of a halogenating agent; c) acidifying said mixture; and d) recovering the substituted .beta.-lactam ester from the reaction mixture; where in the preceding formulae R is hydrogen, C.sub.1 -C.sub.6 alkyl, 4-amino-4-carboxybutyl, phenyl, substituted phenyl, or a group of the formula ##STR25## wherein P is phenyl, C.sub.1 -C.sub.4 lower alkylphenyl, halophenyl, hydroxyphenyl, C.sub.1 -C.sub.4 lower alkoxyphenyl, 2-thienyl, 3-thienyl,
- 2-furyl, 3-furyl, or 1-tetrazyl;
- Z is an oxygen atom, or a sulfur atom;
- n is 0 or 1;
- a is hydrogen or C.sub.1 -C.sub.3 lower alkyl,
- b is hydrogen, C.sub.1 -C.sub.3 lower alkyl, protected hydroxy, amino, or protected amino;
- and when n is 1, P is phenyl, C.sub.1 -C.sub.4 lower alkylphenyl, halophenyl, hydroxyphenyl, C.sub.1 -C.sub.4 lower alkoxyphenyl and
- b is hydrogen or C.sub.1 -C.sub.3 lower alkyl;
- R.sub.1 is hydrogen, an alkali metal cation or a readily removable ester forming moiety; and
- R.sub.2 is C.sub.1 -C.sub.4 lower alkyl, allyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl, or benzyl.
- 2. The process of claim 1 wherein the chlorinating agent is t-butyl hypochlorite.
- 3. The process of claim 1 wherein R.sub.2 is C.sub.1 -C.sub.4 lower alkoxy.
Parent Case Info
This is a division of application Ser. No. 545,451 filed Jan. 30, 1975, now U.S. Pat. No. 3,994,885, which was a division of application Ser. No. 301,694 filed Oct. 27, 1972 as a continuation-in-part of application Ser. No. 222,293 filed Jan. 31, 1972, both now abandoned.
US Referenced Citations (5)
Number |
Name |
Date |
Kind |
3775410 |
Christensen et al. |
Nov 1973 |
|
3778432 |
Pines |
Dec 1973 |
|
3780031 |
Christensen et al. |
Dec 1973 |
|
3780034 |
Christensen et al. |
Dec 1973 |
|
3780037 |
Hazen |
Dec 1973 |
|
Non-Patent Literature Citations (1)
Entry |
J.A.C.S. vol. 93, No. 9, pp. 2308-2312 (5-5-71). |
Divisions (2)
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Number |
Date |
Country |
Parent |
545451 |
Jan 1975 |
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Parent |
301694 |
Oct 1972 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
222293 |
Jan 1972 |
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