Trifluoroacetic acid → HCID 131720153, compound
Reaction equation
C([O:5][C:6]([NH:8][CH2:9][C:10]1[N:17]2[C:13]([S:14][CH:15]=[C:16]2[CH2:18][C:19]([NH2:21])=[O:20])=[CH:12][N:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH:6]([NH:8][CH2:9][C:10]1[N:17]2[C:13]([S:14][CH:15]=[C:16]2[CH2:18][C:19]([NH2:21])=[O:20])=[CH:12][N:11]=1)=[O:5]Participants
3
Procedure
To 0.296 mg of the 5-(tert-butoxycarbonylamino)methylimidazo[5,1-b]thiazole-3-carboxyamide was added 8 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 30 minutes, and then concentrated to dryness under reduced pressure. To the residue were added 50 ml of methylene chloride, 50 ml of tetrahydrofuran and i ml of triethylamine, and the mixture was thoroughly stirred. To this was added a mixture of 2 ml of formic acid and i ml of acetic anhydride, which had been heated to 50° C. for 10 minutes and then cooled to room temperature, and the mixture was stirred for 14 hours. The crystals precipitated were collected by filtration, and dried under reduced pressure to give 0.214 g of the title compound.
Workup
- concentrationconcentrated to dryness under reduced pressure
- additionTo the residue were added 50 ml of methylene chloride, 50 ml of tetrahydrofuran and i ml of triethylamine
- stirringthe mixture was thoroughly stirred
- additionTo this was added
- additiona mixture of 2 ml of formic acid and i ml of acetic anhydride, which
- temperaturehad been heated to 50° C. for 10 minutes
- temperaturecooled to room temperature
- stirringthe mixture was stirred for 14 hours
- customThe crystals precipitated
- filtrationwere collected by filtration
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-0676b4404c984134b8591a28898eeff6
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663162
Reaction notes
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