Sodium Hydroxide → HCID 178521533, compound

HRID 267502Notes

Reaction equation

HRID 267502 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]=[C:14]([OH:16])[NH:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[F:22][C:23]([S:26][CH2:27][C:28](Cl)=[O:29])([F:25])[F:24].[OH-].[Na+]>CC(C)=O.C([O-])(O)=O.[Na+]>[F:22][C:23]([S:26][CH2:27][C:28]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]=[C:14]([OH:16])[NH:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:29])([F:25])[F:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15733943[(Trifluoromethyl)sulfanyl]acetyl chlorideHCID 178508106HCID 178508106, compound

Product 1

HCID 178521533HCID 178521533, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a cold solution (-20°) of 7-amino-3-(5-hydroxy-1,2,4-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic acid (3.39 g., 0.01 mole) in a mixture of acetone (62.5 ml.) and 3% NaHCO3 (62.5 ml.) is added dropwise over a 30 minute period a solution of trifluoromethylmercaptoacetyl chloride (2.24 g., 0.012 mol.) in acetone (20 ml.) The solution is maintained at pH 8 by adding 10% sodium hydroxide as needed. The reaction is stirred for 20 minutes at -15° to -20° and then allowed to warm to room temperature. The solution is washed with ether, covered with ethyl acetate and acidified to pH 2. The aqueous phase is separated and extracted with ethyl acetate. The combined ethyl acetate phases are combined, washed with water, dried, and evaporated to give the title compound.

Workup

  1. temperatureis maintained at pH 8
  2. washThe solution is washed with ether
  3. customThe aqueous phase is separated
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-a3dd9d8e70aa4c23a4250c490d4adeff
Source dataset
uspto-grants-1976_03
Patent number
US03943131

Reaction notes

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