t-Butyl 7-(2-carboxybenzamido)-3-acetoxymethyl-3-cephem-4-carboxylate → t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate

HRID 1730900Notes

Reaction equation

HRID 1730900 reaction equation
C(C1C=CC=CC=1C([NH:8][CH:9]1[C:28](=[O:29])[N:11]2[C:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:14][S:15][C@H:10]12)=O)(O)=O.Cl.NC1C(=O)N2C(C(OC(C)(C)C)=O)=C(COC(=O)C)CS[C@H]12>>[NH2:8][CH:9]1[C:28](=[O:29])[N:11]2[C:12]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[CH2:14][S:15][C@H:10]12

Participants

3

Reactant 2

HCID 70633183t-Butyl 7-(2-carboxybenzamido)-3-acetoxymethyl-3-cephem-4-carboxylateHCID 70633476t-Butyl 7-amino-3-acetoxymethyl-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 15573429t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate

Procedure

In accordance with the procedure of Example 2, t-butyl 7-(2-carboxybenzamido)-3-acetoxymethyl-3-cephem-4-carboxylate is converted to t-butyl 7-amino-3-acetoxymethyl-3-cephem-4-carboxylate hydrochloride, which is converted to the free amine by treatment with NaHCO3 and extraction with chloroform. M.p., ir and nmr spectra are in agreement with an authentic sample prepared according to the method of R. J. Stedman, J. Med. Chem., (1966) p. 444.

Workup

  1. extractionis converted to the free amine by treatment with NaHCO3 and extraction with chloroform
  2. customprepared

Sources & evidence

ORD record
ord-a4f29ab94cb04ae79e26dd605649ea78
Source dataset
uspto-grants-1976_11
Patent number
US03994888

Reaction notes

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