Triethylamine → HCID 70620430, compound

HRID 258685Notes

Reaction equation

HRID 258685 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[O:12][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[F:32][C:33]([F:42])([F:41])[CH2:34][S:35]([CH2:37][C:38](O)=[O:39])=[O:36]>CN(C)C=O>[F:32][C:33]([F:42])([F:41])[CH2:34][S:35]([CH2:37][C:38]([NH:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[O:12][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12)=[O:39])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 205740232-(2,2,2-Trifluoroethanesulfinyl)acetic acidHCID 706204657-Amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 70620430HCID 70620430, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3.4 g (0.01 mol) of 7-amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid in 50 ml of dry dimethylformamide is treated with 2 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 in vacuo and water and ethyl acetate are added to the residue. The layers are separated, the ethyl acetate layer is discarded, fresh 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 combined extracts are washed with water, dried (MgSO4) and evaporated to dryness to give the title compound.

Workup

  1. stirringis stirred an additional hour
  2. customThe reaction mixture is evaporated to dryness in vacuo and water and ethyl acetate
  3. additionare added to the residue
  4. customThe layers are separated
  5. additionfresh ethyl 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 combined extracts are washed with water
  11. dry with materialdried (MgSO4)
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-c40a0088d95349eb85947db0bbf7075e
Source dataset
uspto-grants-1977_07
Patent number
US04034092

Reaction notes

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