Hydrochloric Acid → 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 568845Notes

Reaction equation

HRID 568845 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[CH:10]([NH:12][C:13]1[S:14][C:15]([Br:39])=[C:16]([C:18](=[N:36][O:37][CH3:38])[C:19]([NH:21][CH:22]2[C:34](=[O:35])[N:24]3[C:25]([C:31]([O-:33])=[O:32])=[C:26]([CH2:29][OH:30])[CH2:27][S:28][C@H:23]23)=[O:20])[N:17]=1)=[O:11].[Na+].O.Cl>CC(C)=O.CN(C)C=O>[CH:10]([NH:12][C:13]1[S:14][C:15]([Br:39])=[C:16]([C:18](=[N:36][O:37][CH3:38])[C:19]([NH:21][CH:22]2[C:34](=[O:35])[N:24]3[C:25]([C:31]([OH:33])=[O:32])=[C:26]([CH2:29][O:30][C:6](=[O:7])[NH:5][C:3](=[O:4])[C:2]([Cl:9])([Cl:8])[Cl:1])[CH2:27][S:28][C@H:23]23)=[O:20])[N:17]=1)=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 76400Trichloroacetyl isocyanateHCID 131715344Sodium 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate

Product 1

HCID 1317153467-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acidYield 76.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of trichloroacetyl isocyanate (1.32 g.) in dry acetone (5 ml.) was added dropwise to a solution of sodium 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate (1.9 g.) in dry dimethylformamide at -30° C. and stirred at -40° to -20° C. for 3.5 hrs. Water (20 ml.) was added dropwise to the reaction mixture below -20° C. and the mixture was poured into water (180 ml.). The mixture was adjusted to pH 2 with 6N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diethyl ether and dried to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-trichloroacetylcarbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 1.9 g.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe residue was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-16394a424ce347dabd999a6829cfed7b
Source dataset
uspto-grants-1988_03
Patent number
US04729991

Reaction notes

Loading…