Water → (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide

HRID 2201061

반응식

HRID 2201061 반응식
[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].Cl.[NH2:13][C@@H:14]([C:19]([NH2:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17].CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[C:4]([C:3]1[C:2]([F:1])=[CH:9][C:8]([NH:13][C@H:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:19]([NH2:21])=[O:20])=[CH:7][C:6]=1[F:11])#[N:5]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 7371772,4,6-TrifluorobenzonitrileHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

생성물 1

HCID 67509019(R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide수율 26.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2,4,6-trifluorobenzonitrile (208 mg, 1.32 mmol) in DMSO (2 mL), a solution of D-leucine amide hydrochloride (220 mg, 1.32 mmol) and DIEA (0.688 mL, 3.96 mmol) in DMSO (5 mL) was added. After being stirred at room temperature for 18 h, water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 20-80% EtOAc in hexane to give (R)-2-(4-cyano-3,5-difluorophenylamino)-4-methylpentanamide (92 mg).

후처리

  1. customThe organic phase was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 20-80% EtOAc in hexane

출처 및 근거

ORD 기록
ord-a5e14c12274847e1ab85fbded44b6354
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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