Water → (2S)-2-[(4-bromophenyl)(thien-3-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

HRID 1180389Notes

Reaction equation

HRID 1180389 reaction equation
ClC(Cl)(Cl)C(=N)O[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.[C:21]([CH2:23][NH:24][C:25](=[O:32])[C@@H:26]([OH:31])[CH2:27][CH:28]([CH3:30])[CH3:29])#[N:22].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.O>ClCCl>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([CH:5]([C:6]2[CH:10]=[CH:9][S:8][CH:7]=2)[O:31][C@@H:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[C:25]([NH:24][CH2:23][C:21]#[N:22])=[O:32])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 69473113(4-Bromophenyl)(thien-3-yl)methyl 2,2,2-trichloroethammidoateHCID 86605382HCID 86605382, compound

Product 1

HCID 86605381(2S)-2-[(4-bromophenyl)(thien-3-yl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromophenyl)(thien-3-yl)methyl 2,2,2-trichloroethanimidoate from step 2 (970 mg, 2.36 mmol) in dichloromethane (12 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide (402 mg, 2.36 mmol) and camphorsulfonic acid (137 mg, 0.59 mmol). The reaction was stirred overnight at room temperature and the resulting mixture was poured into water. The aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried and evaporated and the crude residue was chromatographed on silica gel using 50% ethyl acetate in hexanes to afford the title compound.

Workup

  1. extractionThe aqueous layer was extracted 3 times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated
  5. customthe crude residue was chromatographed on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c728fa1684cb449d983a5f3f836d5761
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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