Claims
- 1. A compound of the formula ##STR57## wherein R is a carboxylic acid protecting group; R.sub.1 is
- (1) an imido group of the formula ##STR58## wherein R.sub.2 is C.sub.2 -C.sub.4 alkenylene, C.sub.2 -C.sub.4 alkylene, 1,2-phenylene, 1,2-cyclohexenylene; or
- (2) an amido group of the formula ##STR59## wherein R.sub.3 is (a) hydrogen, C.sub.1 -C.sub.3 alkyl, halomethyl, cyanomethyl or 3-(2-chlorophenyl)-5-methylisoxazol-4-yl;
- (b) benzyloxy, 4-nitrobenzyloxy, 2,2,2-trichloroethoxy, tert-butoxy, or 4-methoxybenzyloxy;
- (c) the group R" wherein R" is phenyl or phenyl substituted with 1 or 2 substituents independently selected from the group consisting of halo, protected hydroxy, nitro, cyano, trifluoromethyl, C.sub.1 -C.sub.3 alkyl, and C.sub.1 -C.sub.4 alkoxy;
- (d) an arylalkyl group of the formula
- R.degree.--(Q).sub.m --CH.sub.2 --
- wherein R.degree. is R" as defined above, 2-thienyl, 3-thienyl or 1,4-cyclohexadienyl, m is 0 or 1, and Q is O or S subject to the limitation that when m is 1, R.degree. is R";
- (e) a substituted arylalkyl group of the formula ##STR60## wherein R.degree. is R" as defined above, 2-thienyl, 3-thienyl or 1,4-cyclohexadienyl, and W is protected hydroxy or protected amino;
- (3) an imido group of the formula ##STR61## wherein R.degree. and m are as defined hereinabove and R.sub.2 ' is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.3 alkoxy, or trichloroethoxy; or R.sub.1 is
- (4) an imidazolidinyl group of the formula ##STR62## wherein R.degree. is R" as defined above, 2-thienyl, 3-thienyl or 1,4-cyclohexadienyl, and Y is acetyl or nitroso;
- and X is
- (1) a group of the formula --OR.sub.4 wherein R.sub.4 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.6 haloalkyl, or an aryl(C.sub.1 -C.sub.3 alkyl) group wherein aryl is naphthyl or phenyl optionally substituted with chloro, bromo, methoxy or nitro;
- (2) a group of the formula --SR.sub.5 wherein R.sub.5 is C.sub.1 -C.sub.6 alkyl, or an aryl or aryl(C.sub.1 -C.sub.3 alkyl) group wherein aryl is naphthyl or phenyl optionally substituted with chloro, bromo, methoxy or nitro; or
- (3) a group of the formula ##STR63## wherein (a) R.sub.6 is hydrogen and R.sub.7 is hydrogen, R" as defined hereinabove, or a group of the formula --NHR.sub.8 wherein R.sub.8 is aminocarbonyl, C.sub.1 -C.sub.3 alkylaminocarbonyl, C.sub.1 -C.sub.3 alkylcarbonyl, C.sub.1 -C.sub.3 alkoxycarbonyl or tosyl; or
- (b) R.sub.6, R.sub.7 and the nitrogen atom to which they are bonded taken together form an imido group of the formula ##STR64## wherein R.sub.2 is as defined hereinabove.
- 2. The compound of claim 1 wherein R is methyl, tert-butyl, benzyl, 4-methoxybenzyl, C.sub.2 -C.sub.4 alkanoyloxymethyl, 2-iodoethyl, 4-nitrobenzyl, diphenylmethyl (benzhydryl), phenacyl, 4-halophenacyl, dimethylallyl, 2,2,2-trichloroethyl, tri(C.sub.1 -C.sub.3 alkyl)silyl or succinimidomethyl.
- 3. The compound of claim 1 wherein X is a group of the formula --OR.sub.4.
- 4. The compound of claim 3 wherein R.sub.4 is hydrogen.
- 5. The compound of claim 1 wherein X is a group of the formula --SR.sub.5.
- 6. The compound of claim 1 wherein X is a group of the formula ##STR65##
- 7. The compound of claim 6 wherein R.sub.6 is hydrogen and R.sub.7 is hydrogen, R", or a group of the formula --NHR.sub.8.
- 8. The compound of claim 6 wherein R.sub.6, R.sub.7, and the nitrogen atom to which they are bonded taken together form an imido group of the formula ##STR66##
- 9. The compound of claim 1 wherein R.sub.1 is an imido group of the formula ##STR67##
- 10. The compound of claim 9 wherein R.sub.1 is phthalimido.
- 11. The compound of claim 1 wherein R.sub.1 is an imido group of the formula ##STR68##
- 12. The compound of claim 1 wherein R.sub.1 is an imidazolidinyl group of the formula ##STR69##
- 13. The compound of claim 1 wherein R.sub.1 is an amido group of the formula ##STR70##
- 14. The compound of claim 13 wherein R.sub.3 is an arylalkyl group of the formula R.degree. --(Q).sub.m --CH.sub.2 --.
- 15. The compound of claim 14 wherein R.sub.3 is benzyl or phenoxymethyl.
- 16. The compound of claim 14 wherein R.sub.3 is 2-thienylacetamido.
- 17. The compound of claim 13 wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.3 alkyl, halomethyl, or 3-(2-chlorophenyl)-5-methylisoxazol-4-yl.
- 18. The compound of claim 13 wherein R.sub.3 is benzyloxy, 4-nitrobenzyloxy, 2,2,2-trichloroethoxy, tert-butoxy or 4-methoxybenzyloxy.
- 19. The compound of claim 13 wherein R.sub.3 is the group --R", wherein R" is phenyl or phenyl substituted with 1 or 2 substituents independently selected from the group consisting of halo, protected hydroxy, nitro, cyano, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.4 alkoxy.
- 20. The compound of claim 13 wherein R.sub.3 is a substituted arylalkyl group of the formula ##STR71##
CROSS-REFERENCE TO RELATED APPLICATION
This is a division, of application Ser. No. 673,036 filed Apr. 2, 1976, now U.S. Pat. No. 4,052,387 which is a continuation-in-part of application Ser. No. 632,733, filed Nov. 19, 1975, now abandoned, which is a continuation-in-part of application Ser. No. 536,280, filed Dec. 24, 1974, now abandoned.
US Referenced Citations (7)
Non-Patent Literature Citations (9)
Entry |
Chou et al., J. American Chem. Soc. 96, 1609 (1974). |
Chou, Tet. Letters #9, pp. 725-728 (1974). |
Sammes et al., Chem. Revs., 1976, vol. 76, 113-155. |
Ishimaru et al. Bull. Chem. Soc. Japan 48, 2989-70 (1975). |
Koppel et al. Chem. Abs. 82, 170536q (1975). |
Terao et al. J. Chem. Soc. (D) 1304 (1972). |
Kukolja et al. II, Angew. Chem. 12, 67-68 (1973). |
Tuleen et al. Chem. Ind. 1966, 1555. |
Huff et al. Chem. Abs. 80, 95380n (1974). |
Divisions (1)
|
Number |
Date |
Country |
Parent |
673036 |
Apr 1976 |
|
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
632733 |
Nov 1975 |
|
Parent |
536280 |
Dec 1974 |
|