Trifluoroacetic anhydride → HCID 54174090, compound

HRID 1378030Notes

Reaction equation

HRID 1378030 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[O:14]=[C:15]1[N:21]2[CH2:22][CH2:23][C@H:20]2[C:19]2=[C:24]([C:27]([NH2:29])=O)[N:25]=[CH:26][N:18]2[C:17]2[CH:30]=[CH:31][S:32][C:16]1=2>O1CCOCC1.N1C=CC=CC=1>[O:14]=[C:15]1[N:21]2[CH2:22][CH2:23][C@H:20]2[C:19]2=[C:24]([C:27]#[N:29])[N:25]=[CH:26][N:18]2[C:17]2[CH:30]=[CH:31][S:32][C:16]1=2

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 53747560HCID 53747560, compound

Product 1

HCID 54174090HCID 54174090, compoundYield 1,658.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

5.75 ml (41.3 mmol) of trifluoroacetic anhydride were added dropwise at 5°-8° to a suspension of 11.05 g (40.:2 mmol) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carboxamide in 55 ml of dioxan and 7 ml of pyridine. The beige solution obtained was stirred at 50° for 2.5 hours and subsequently poured into 50 ml of ice-water. Extraction with methylene chloride (four times), drying over sodium sulfate, filtration and evaporation yielded a pale brown residue which was chromatographed (silica gel, methylene chloride/methanol 10:1). There were obtained 8.5 g (82%) of (S)-8-oxo-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepine-1-carbonitrile as a white powder of m.p. 211°-213°.

Workup

  1. customThe beige solution obtained
  2. extractionExtraction with methylene chloride (four times)
  3. dry with materialdrying over sodium sulfate, filtration and evaporation
  4. customyielded a pale brown residue which
  5. customwas chromatographed (silica gel, methylene chloride/methanol 10:1)

Sources & evidence

ORD record
ord-b24cda78172c4e8899494571d1b89bee
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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