Dimethylformamide → HCID 178514770, compound

HRID 839016Notes

Reaction equation

HRID 839016 reaction equation
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH:9]([S:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)[CH2:10][CH2:11][S:12](=[O:15])(=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12.CN(C)C=O.[F:32][C:33]([F:42])([F:41])[CH2:34][S:35]([CH2:37][C:38](O)=[O:39])=[O:36]>C(N(CC)CC)C>[F:32][C:33]([F:42])([F:41])[CH2:34][S:35]([CH2:37][C:38]([NH:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH:9]([S:16][C:17]3[NH:18][N:19]=[N:20][N:21]=3)[CH2:10][CH2:11][S:12](=[O:14])(=[O:15])[NH2:13])[CH2:7][S:8][C@H:3]12)=[O:39])=[O:36]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 205740232-(2,2,2-Trifluoroethanesulfinyl)acetic acidHCID 178508099HCID 178508099, compound

Product 1

HCID 178514770HCID 178514770, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A suspension of 4.17 g. (0.01 mol.) of 7-amino-3-[1-(2-sulfamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 50 ml. of dry dimethylformamide is treated with 2 ml. of triethylamine and the mixture is stirred for 15 minutes at 25°. A slight excess of 0.01 mol. of the activated ester of 2,2,2-trifluoroethylsulfinylacetic acid is added to the mixture and it is stirred an additional hour. The reaction mixture is evaporated to dryness and water and ethyl acetate are added to the residue. The layers are separated, ethyl acetate is added to the aqueous phase and it is acidified to pH 2.5 by addition of 6N hydrochloric acid. The mixture is filtered, the layers are separated and the aqueous phase is extracted with ethyl acetate. The extract is washed with water, dried (MgSO4) and evaporated to dryness to give the title compound.

Workup

  1. additionA suspension of 4.17 g
  2. customThe reaction mixture is evaporated to dryness and water and ethyl acetate
  3. additionare added to the residue
  4. customThe layers are separated
  5. additionethyl acetate is added to the aqueous phase and it
  6. additionis acidified to pH 2.5 by addition of 6N hydrochloric acid
  7. filtrationThe mixture is filtered
  8. customthe layers are separated
  9. extractionthe aqueous phase is extracted with ethyl acetate
  10. washThe extract is washed with water
  11. dry with materialdried (MgSO4)
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-6ae6ae2873604df7a5412c3c55ede64e
Source dataset
uspto-grants-1978_06
Patent number
US04093723

Reaction notes

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