Water → N-[(1S,2R)-2-(4-Benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

HRID 2220598Notes

Reaction equation

HRID 2220598 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([C@@H:21]([OH:31])[C@@H:22]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH3:23])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1C=CC=CC=1.O>C(OCC)(=O)C>[CH2:14]([O:13][C:12]1[CH:11]=[CH:10][C:9]([C@@H:21]([OH:31])[C@@H:22]([NH:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])[CH3:23])=[CH:8][C:7]=1[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86611767N-[(1S,2R)-2-(3-Amino-4-benzyloxyphenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

Product 1

HCID 86611768N-[(1S,2R)-2-(4-Benzyloxy-3-methanesulfonylaminophenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Methanesulfonyl chloride (14 mL) was added to a mixture of N-[(1S,2R)-2-(3-amino-4-benzyloxyphenyl)-2-hydroxy-1-methylethyl]-2,2,2-trifluoroacetamide (62 g) and pyridine (34 mL) in ethyl acetate (558 mL) at room temperature with stirring, and the mixture was stirred at 40° C. for 1 hr. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed successively with 1 mol/L hydrochloric acid, water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from n-hexane/ethyl acetate to afford the title compound (42 g).

Workup

  1. stirringthe mixture was stirred at 40° C. for 1 hr
  2. customThe organic layer was separated
  3. washwashed successively with 1 mol/L hydrochloric acid, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-99ccd83def7845c7b5ecdf54c164dfbf
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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