Bromomethyl acetate → HCID 178476668, compound

HRID 1658488Notes

Reaction equation

HRID 1658488 reaction equation
[F:1][C:2]([S:5][CH2:6][C:7]([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([O-:27])=[O:26])=[C:14]([CH:17]([S:19][C:20]3[NH:24][N:23]=[N:22][N:21]=3)[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8])([F:4])[F:3].[Na+].[C:31]([O:34][CH2:35]Br)(=[O:33])[CH3:32]>CN(C=O)C.O>[F:1][C:2]([S:5][CH2:6][C:7]([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:25]([O:27][CH2:35][O:34][C:31](=[O:33])[CH3:32])=[O:26])=[C:14]([CH:17]([S:19][C:20]3[NH:21][N:22]=[N:23][N:24]=3)[CH3:18])[CH2:15][S:16][C@H:11]12)=[O:8])([F:4])[F:3]

Participants

5

Reactant 2

HCID 68536Bromomethyl acetateHCID 178477395HCID 178477395, compound

Product 1

HCID 178476668HCID 178476668, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold solution of sodium 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate (738 mg, 1.5 mmol) in dry DMF (10 ml) is added a solution of bromomethyl acetate (253 mg, 1.65 mmol) in DMF (1 ml). The reaction is stirred for 30 minutes at 0°C and 90 minutes at room temperature. The reaction is diluted with water and the aqueous mixture is extracted with ethyl acetate. The extracts are washed with water, dried and evaporated to give acetoxymethyl 7-trifluoromethylmercaptoacetamido-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate. The product is dissolved in ethyl acetate and is precipitated by the addition of petroleum ether.

Workup

  1. extractionthe aqueous mixture is extracted with ethyl acetate
  2. washThe extracts are washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-45e22440da694450ac3aff358970dafb
Source dataset
uspto-grants-1976_06
Patent number
US03965099

Reaction notes

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