Methyl fluorosulfate → HCID 70634328, compound

HRID 1606499Notes

Reaction equation

HRID 1606499 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]([NH:20][CH:21]2[C:45](=[O:46])[N:23]3[C:24]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:25]([OH:28])[CH2:26][S:27][C@H:22]23)=[O:19])=[CH:12][CH:11]=1.FS(OC)(=O)=O>CN(P(N(C)C)(N(C)C)=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]([NH:20][CH:21]2[C:45](=[O:46])[N:23]3[C:24]([C:29]([O:31][CH:32]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:25]([O:28][CH3:1])[CH2:26][S:27][C@H:22]23)=[O:19])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 9870Methyl fluorosulfateHCID 2724682Lithium diisopropylamideHCID 131710152HCID 131710152, compound

Product 1

HCID 70634328HCID 70634328, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 60 mg. of lithium diisopropylamide in 10 cc. of HMPA is cooled to 0°C. and 260 mg. of diphenylmethyl 7-(4-chlorophenylthio)acetamido-3-hydroxy-3-cephem-4-carboxylate is added in one portion. After stirring the reaction mixture for 1 minute, 70 mg. of methyl fluorosulfonate is added, and stirring is continued for 30 minutes. The reaction mixture is poured into 50 cc. of ethyl acetate, washed with water, and dried. Removal of the solvent under reduced pressure provides diphenylmethyl 7-(4-chlorophenylthio)acetamido-3-methoxy-3-cephem-4-carboxylate.

Workup

  1. stirringstirring
  2. waitis continued for 30 minutes
  3. additionThe reaction mixture is poured into 50 cc
  4. washof ethyl acetate, washed with water
  5. customdried
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-73a2d3f61c2247f8be099a53f124fc49
Source dataset
uspto-grants-1976_04
Patent number
US03953438

Reaction notes

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