Acetone → HCID 131710311, compound

HRID 1657729Notes

Reaction equation

HRID 1657729 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12.[S:15]([CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21])([OH:18])(=[O:17])=[O:16].CC(C)=O.C(=O)(O)[O-].[Na+]>O>[S:15]([CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20]([NH:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([Cl:9])[CH2:7][S:8][C@H:3]12)=[O:21])([OH:18])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 13127332α-(Chlorocarbonyl)benzenemethanesulfonic acidHCID 23620956HCID 23620956, compound

Product 1

HCID 131710311HCID 131710311, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The α-sulfo-acylamido-3-halo-cephem compounds of the Formula I wherein Q is a sulfo group (--SO3H) are prepared by following the acylation procedures employed for the preparation of α-sulfobenzylpenicillins described by U.S. Patent No. 3,660,379 and in the J. Med. Chem., 15 (11), 11-5 (1972); ibid, p. 1108. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid is reacted with α-sulfophenylacetyl chloride in a mixture acetone and water containing an excess of sodium bicarbonate to yield 7-(α-sulfophenylacetamido)-3-chloro-3-cephem-4-carboxylic acid. Examples of α-sulfoacylamido-3-halo-cephems of the present invention are,

Workup

  1. customare prepared
  2. customemployed for the preparation of α-sulfobenzylpenicillins

Sources & evidence

ORD record
ord-986e4b98e21a4c60ba2f3eaf7f1894a2
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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