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

HRID 1180389노트

반응식

HRID 1180389 반응식
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

참가 물질

6

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c728fa1684cb449d983a5f3f836d5761
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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