Trifluoroacetic anhydride → HCID 54313191, compound

HRID 1378244Notes

Reaction equation

HRID 1378244 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][CH2:24][C@H:20]2[C:19]2=[C:25]([C:28]([NH2:30])=O)[N:26]=[CH:27][N:18]2[C:17]2[CH:31]=[CH:32][S:33][C:16]1=2>O1CCOCC1.N1C=CC=CC=1>[O:14]=[C:15]1[N:21]2[CH2:22][CH2:23][CH2:24][C@H:20]2[C:19]2=[C:25]([C:28]#[N:30])[N:26]=[CH:27][N:18]2[C:17]2[CH:31]=[CH:32][S:33][C:16]1=2

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 54419029HCID 54419029, compound

Product 1

HCID 54313191HCID 54313191, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

4.44 ml (31.9 mmol) of trifluoroacetic anhydride were added dropwise at 5°-8° to a suspension of 8.98 g (31.1 mmol) of (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carboxamide in 50 ml of dioxan and 5.4 ml of pyridine. The beige solution obtained was stirred at 50° for 2.5 hours and subsequently poured into 220 ml of ice-water. The resulting precipitate was filtered off. After drying at 70°/10 Torr there were obtained 6.78 g (80%) of (S)-10,11,12,12a-tetrahydro-8-oxo-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine-1-carbonitrile as a white powder of m.p. 249°-251°.

Workup

  1. customThe beige solution obtained
  2. filtrationThe resulting precipitate was filtered off
  3. customAfter drying at 70°/10 Torr there

Sources & evidence

ORD record
ord-e8264862a3ae41bb900b899e70c41219
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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