Water → HCID 58696315, compound

HRID 1178346Notes

Reaction equation

HRID 1178346 reaction equation
[C:1]1([O:7][C:8](=[O:34])[N:9]([C@:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)([CH2:22][CH2:23][CH2:24][OH:25])[CH2:12][N:13]([CH3:21])[C:14](=[O:20])[CH2:15][C:16]([F:19])([F:18])[F:17])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[C:1]1([O:7][C:8](=[O:34])[N:9]([C@:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)([CH2:22][CH2:23][CH:24]=[O:25])[CH2:12][N:13]([CH3:21])[C:14](=[O:20])[CH2:15][C:16]([F:19])([F:17])[F:18])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 58696376HCID 58696376, compound

Product 1

HCID 58696315HCID 58696315, compoundYield 115.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under argon, phenyl[1-(3,3,3-trifluoro-N-methylpropanamido)-2-(S)-(3,4-dichlorophenyl)-5-hydroxy-pentan-2-yl]methylcarbamate (100 mg) was dissolved in anhydrous dimethyl sulfoxide (1.0 mL). At room temperature, triethylamine (0.16 mL) and pyridine sulfur trioxide complex (94 mg) were added thereto, and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, to thereby give the title compound (115 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over sodium sulfate anhydrate
  4. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e7bcb70daec4869b51fcc67aad9d7b0
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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