2-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine → 7-[2-(2-Thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid

HRID 443544

Reaction equation

HRID 443544 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20]CC3C=CC([N+]([O-])=O)=CC=3)=[O:19])=[C:14](O)[CH2:15][S:16][C@H:11]12)=[O:8].ClC(F)C(N(CC)CC)(F)[F:36]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([OH:20])=[O:19])=[C:14]([F:36])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amineHCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 705600817-[2-(2-Thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 325 mg. (0.7 mmole) of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate in 10 ml. of methylene chloride was slowly added an equivalent amount of N-(2-chloro-1,1,2-trifluoroethyl) diethylamine. The reaction mixture was heated for 30 minutes under gentle reflux and was then evaporated to dryness in vacuo. The residue was dissolved in a mixture of ethyl acetate-water and the organic layer was separated. The organic layer was washed with 5% hydrochloric acid, water and brine and was then dried. The dried reaction product solution was concentrated to a small volume and n-hexane was added to precipitate, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-fluoro-3-cephem-4-carboxylate.

Workup

  1. temperatureThe reaction mixture was heated for 30 minutes
  2. temperatureunder gentle reflux
  3. customwas then evaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in a mixture of ethyl acetate-water
  5. customthe organic layer was separated
  6. washThe organic layer was washed with 5% hydrochloric acid, water and brine
  7. customwas then dried
  8. customThe dried reaction product solution
  9. concentrationwas concentrated to a small volume and n-hexane
  10. additionwas added
  11. customto precipitate

Sources & evidence

ORD record
ord-98fbd01fc10143498ca6389d234b97cc
Source dataset
uspto-grants-1981_04
Patent number
US04260745

Linked notes

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