Water → HCID 88605977, compound

HRID 2108208Notes

Reaction equation

HRID 2108208 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25]CC4C=CC(OC)=CC=4)=[O:24])=[C:15](OS(C)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH-:37].[Na+].O.CN(C)[CH:42]=[O:43]>C(N(C(C)C)CC)(C)C>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:23]([O:25][C:1]4[CH:6]=[CH:5][C:4]([O:43][CH3:42])=[CH:3][CH:2]=4)=[O:24])=[C:15]([SH:37])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 28015Sodium hydrosulfideHCID 14538788HCID 14538788, compound

Product 1

HCID 88605977HCID 88605977, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 34.4 g (64.5 mM) of 4-methoxybenzyl 7β-phenylacetamido-3-methanesulfonyloxy-3-cephem-4-carboxylate in 100 ml of N,N-dimethylformamide were added at -30° C. a solution of 5.68 g (71.0 mM) of 70% sodium hydrosulfide in 50 ml of N,N-dimethylformamide and 12.5 g (96.9 mM) of diisopropylethylamine, and the mixture was stirred for 30 minutes. After the reaction, 500 ml of water was added and the mixture was washed with 300 ml of ethyl acetate. The aqueous layer was adjusted to pH 2 to 3 with 0.5% hydrochloric acid and extracted with 1 l of ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution (300 ml×3) and dried over anhydrous magnesium sulfate. The solvent was evaporate and n-hexane was added to the residue for powdering to give 22.0 g of 4-methoxyphenyl 7β-phenylacetamido-3-mercapto-3-cephem-4 -carboxylate.

Workup

  1. additionwas added
  2. washthe mixture was washed with 300 ml of ethyl acetate
  3. extractionextracted with 1 l of ethyl acetate
  4. washthe extract was washed with a saturated aqueous sodium chloride solution (300 ml×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporate
  7. additionn-hexane was added to the residue

Sources & evidence

ORD record
ord-0507d6446913418aa17c8909348c58d9
Source dataset
uspto-grants-1990_06
Patent number
US04937332

Reaction notes

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