Water → (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide

HRID 2201050

반응식

HRID 2201050 반응식
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([O:18][CH2:19][C@H:20]([C:22]([NH2:24])=[O:23])[NH2:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.O>CS(C)=O.CCOC(C)=O>[CH2:11]([O:18][CH2:19][C@@H:20]([NH:21][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([Br:1])[CH:9]=1)[C:22]([NH2:24])=[O:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1189392-Bromo-4-fluorobenzonitrileHCID 58987402O-benzyl-D-serinamide

생성물 1

HCID 67509048(R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide수율 17.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-bromo-4-fluorobenzonitrile (200 mg, 1.00 mmol), O-benzyl-D-serinamide (290 mg, 1.49 mmol) and DIEA (0.466 mL, 2.68 mmol) in DMSO (3 mL) was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 0-60% EtOAc in hexane to give (R)-3-(benzyloxy)-2-(3-bromo-4-cyanophenylamino)propanamide (66 mg).

후처리

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column
  6. washeluted with 0-60% EtOAc in hexane

출처 및 근거

ORD 기록
ord-7b1a324529b0441bba81e652b653dea6
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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