Water → 2-Amino-2-[3-(trifluoromethyl)phenyl]ethyl carbamate
Reaction equation
[OH:1][CH2:2][CH:3]([NH:14]C(=O)OC(C)(C)C)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.ClS([N:26]=[C:27]=[O:28])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[C:27](=[O:28])([O:1][CH2:2][CH:3]([NH2:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)[NH2:26]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
Of the compound from Example 59A, 93 mg (0.31 mmol) were introduced in 4 ml of acetonitrile under argon. At −15° C., 37 μl (0.43 mmol) of chlorosulphonyl isocyanate were added dropwise. After 30 min, the reaction solution was admixed with 8 ml of water and heated at 60° C. overnight. The reaction mixture was cooled and introduced into saturated sodium hydrogen carbonate solution. It was extracted with twice 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 66 mg (64% of theory) of the title compound in 73% purity.
Workup
- temperatureThe reaction mixture was cooled
- extractionIt was extracted with twice 10 ml of ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- filtrationfiltered
- customfreed from the solvent on a rotary evaporator
- customDrying in an HV
Sources & evidence
- ORD record
- ord-499dad5bce914a73aefe165188c289e8
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202895B2
Reaction notes
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