Ammonia → tert-Butyl 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethylcarbamate

HRID 1961455Notes

Reaction equation

HRID 1961455 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23])=[CH:18][CH:17]=1)=[N:4]OS(C1C=CC(C)=CC=1)(=O)=O.[NH3:34]>C(Cl)Cl.CO.O>[F:33][C:2]([F:32])([F:1])[C:3]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH3:23])=[CH:18][CH:17]=2)[N:4]=[N:34]1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 86661978tert-Butyl 1-(4-(2,2,2-trifluoro-1-(tosyloxyimino)ethyl)phenyl)ethylcarbamate

Product 1

HCID 68071561tert-Butyl 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethylcarbamateYield 46%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-(4-(2,2,2-trifluoro-1-(tosyloxyimino)ethyl)phenyl)ethylcarbamate (400 mg, 0.82 mmol) was dissolved in CH2Cl2 (5 ml). Ammonia in MeOH (7 ml, 7M) was added and the resulting mixture was stirred at room temperature for 7 days. The reaction was then diluted with water (50 ml) and extracted with CH2Cl2 (2*25 ml). Combined organics were dried over MgSO4, filtered and evaporated. The product was purified by flash chromatography using Pet. Ether/EtOAc (3:1) as eluent to give 125 mg (46%) of the title compound as white solids.

Workup

  1. extractionextracted with CH2Cl2 (2*25 ml)
  2. dry with materialCombined organics were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-b05f332660d34819814df5b62938356d
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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