Water → HCID 86694779, compound

HRID 709145Notes

Reaction equation

HRID 709145 reaction equation
[Cl:1]S([N:5]=[C:6]=[O:7])(=O)=O.[OH:8][CH2:9][C@@H:10]([NH:22]C(=O)OC(C)(C)C)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.O>C(#N)C>[ClH:1].[C:6](=[O:7])([O:8][CH2:9][C@@H:10]([NH2:22])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=1)[NH2:5]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 67447948HCID 67447948, compound

Product 1

HCID 86694779HCID 86694779, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At −15° C., 51 μl (0.70 mmol) of chlorosulphonyl isocyanate were added slowly to a solution of 160 mg (0.50 mmol) of (2S)-tert-butyl {1-hydroxy-3-[3-(trifluoromethyl)phenyl]propan-2-yl}carbamate (for the preparation see US patent application 2008/0242694, Example [0464]) in 7.6 ml of acetonitrile. The reaction mixture was stirred at RT for 1 h, 1 ml of water was then added and the mixture was heated at 60° C. overnight. An analytical sample showed complete conversion into the target product according to LC/MS. After cooling to RT, the volatile components were removed on a rotary evaporator and finally under high vacuum. The residue (80 mg, 53% of theory) corresponded to the title compound.

Workup

  1. temperaturethe mixture was heated at 60° C. overnight
  2. temperatureAfter cooling to RT
  3. customthe volatile components were removed on a rotary evaporator and finally under high vacuum

Sources & evidence

ORD record
ord-8ed5db6f169b4095966fef3f50f60bf3
Source dataset
uspto-grants-2015_11
Patent number
US09180120B2

Reaction notes

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