Sodium Hydroxide → HCID 68148270, compound

HRID 267494Notes

Reaction equation

HRID 267494 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[S:12][CH:13]=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12.[F:21][C:22]([F:30])([F:29])[S:23]([CH2:25][C:26](Cl)=[O:27])=[O:24].[OH-].[Na+]>C(=O)(O)[O-].[Na+].CC(C)=O>[F:21][C:22]([F:30])([F:29])[S:23]([CH2:25][C:26]([NH:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[S:12][CH:13]=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12)=[O:27])=[O:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 21554927HCID 21554927, compound

Product 1

HCID 68148270HCID 68148270, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3.1 g (0.009 mol) of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid in 60 ml of 3 percent aqueous sodium bicarbonate is added 60 ml of acetone. The solution is cooled to -15° and 1.94 g (0.010 mol) of trifluoromethylsulfinylacetyl chloride in 20 ml of acetone is added over a 10-minute period. The reaction mixture is stirred at -15° for 30 minutes while maintaining the pH at 7.6-8.0 by addition of 10 percent sodium hydroxide, then at 25° for one hour. The reaction mixture is extracted once with ether and the aqueous phase is acidified to pH 2.5 with dilute hydrochloric acid and extracted with ethyl acetate. The organic extracts are dried (MgSO4) and concentrated in vacuo to give the title compound.

Workup

  1. temperatureThe solution is cooled to -15°
  2. temperaturewhile maintaining the pH at 7.6-8.0
  3. waitat 25° for one hour
  4. extractionThe reaction mixture is extracted once with ether
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic extracts are dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-829d22dce4ed4d23955c18433c0e8d74
Source dataset
uspto-grants-1976_03
Patent number
US03943128

Reaction notes

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