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

HRID 1414336Notes

Reaction equation

HRID 1414336 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-881c18db8e9d43f59474862eb6ff4e6c
Source dataset
uspto-grants-1977_01
Patent number
US04001239

Reaction notes

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