Dimethylformamide → HCID 178513910, compound

HRID 27133Notes

Reaction equation

HRID 27133 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH:9]([S:15][C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12.CN(C)C=O.[F:31][C:32]([S:35][CH2:36][C:37](O)=[O:38])([F:34])[F:33]>C(N(CC)CC)C>[F:31][C:32]([S:35][CH2:36][C:37]([NH:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH:9]([S:15][C:16]3[NH:17][N:18]=[N:19][N:20]=3)[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12)=[O:38])([F:34])[F:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33862532-[(Trifluoromethyl)sulfanyl]acetic acidHCID 1785139097-Amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 178513910HCID 178513910, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A suspension of 3.85 g. (0.01 mol.) of 7-amino-3-[1-(2-carbamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 50 ml. of dry dimethylformamide was treated with 2 ml. of triethylamine and the mixture was stirred for 15 minutes at 25°. The activated ester of trifluoromethylmercaptoacetic acid (2.57 g., 0.016 mol.) was added to the mixture and it was stirred an additional hour. The reaction mixture was evaporated to dryness and water and ethyl acetate were added to the residue. The layers were separated, ethyl acetate was added to the aqueous phase and it was acidified to pH 2.5 by addition of 6N hydrochloric acid. The mixture was filtered, the layers were separated and the aqueous phase was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and evaporated to dryness to give the title compound.

Workup

  1. additionA suspension of 3.85 g
  2. customThe reaction mixture was evaporated to dryness and water and ethyl acetate
  3. additionwere added to the residue
  4. customThe layers were separated
  5. additionethyl acetate was added to the aqueous phase and it
  6. additionwas acidified to pH 2.5 by addition of 6N hydrochloric acid
  7. filtrationThe mixture was filtered
  8. customthe layers were separated
  9. extractionthe aqueous phase was extracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materialdried (MgSO4)
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-2b641d84180448b3873fe599834e67dc
Source dataset
uspto-grants-1980_09
Patent number
US04220644

Reaction notes

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