Sodium Bicarbonate → HCID 131710310, compound

HRID 443532Notes

Reaction equation

HRID 443532 reaction equation
C([C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:9](Cl)=[O:10])[C:6](Cl)=[O:7])(C)(C)C.C(C(C1SC=CC=1)(C(Cl)=O)C(Cl)=[O:24])(C)(C)C.C(=O)(O)[O-].[Na+].[NH2:39][CH:40]1[C:55](=[O:56])[N:42]2[C:43]([C:48]([O:50]C(C)(C)C)=[O:49])=[C:44]([Cl:47])[CH2:45][S:46][C@H:41]12>CC(C)=O>[C:9]([CH:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:6]([NH:39][CH:40]1[C:55](=[O:56])[N:42]2[C:43]([C:48]([OH:50])=[O:49])=[C:44]([Cl:47])[CH2:45][S:46][C@H:41]12)=[O:7])([OH:10])=[O:24]

Participants

6

Reactant 4

HCID 516892Sodium Bicarbonate2×HCID 21163678HCID 21163678, compound2×HCID 54130171HCID 54130171, compoundHCID 69648582HCID 69648582, compound

Product 1

HCID 131710310HCID 131710310, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compounds of the Formula I wherein Q is a carboxylic acid group can be prepared for example, by the acylation of a 3-halo-3-cephem nucleus ester with tert-butyl phenylmalonic acid chloride, or with tert-butyl 2-thienylmalonic acid chloride in the presence of a hydrogen halide acceptor such as sodium bicarbonate. For example, tert-butyl 7-amino-3-chloro-3-cephem-4-carboxylate is reacted with 2 equivalents of tert-butyl phenylmalonyl chloride in acetone at a temperature of about 5° C. and in the presence of excess sodium bicarbonate to provide, tert-butyl 7-(α-tert-butyloxycarboxylphenylacetamido)-3-chloro-3-cephem-4-carboxylate. Removal of both tert-butyl ester groups with 90% formic acid provides the diacid, 7-(α-carboxyphenylacetamido)-3-chloro-3-cephem-4-carboxylic acid.

Workup

  1. customto provide
  2. customRemoval of both tert-butyl ester groups with 90% formic acid

Sources & evidence

ORD record
ord-ddc4ad8bdbd6428c8476c389c57dbbf7
Source dataset
uspto-grants-1981_04
Patent number
US04260745

Reaction notes

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