Methanol → (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide

HRID 718923노트

반응식

HRID 718923 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][N:7]([C@@H:30]([CH3:38])[CH:31]([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])[C:8](=[O:29])[C@@H:9]([NH:11]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH3:10])[C:3]2[CH:39]=[CH:40][CH:41]=[CH:42][C:2]1=2.N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:11][C@@H:9]([CH3:10])[C:8]([N:7]([CH2:6][C:4]1[C:3]2[CH:39]=[CH:40][CH:41]=[CH:42][C:2]=2[S:1][CH:5]=1)[C@@H:30]([CH3:38])[CH:31]([O:35][CH2:36][CH3:37])[O:32][CH2:33][CH3:34])=[O:29]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 86652579(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamate

생성물 1

HCID 67075261(S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide수율 75.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

(9H-Fluoren-9-yl)methyl (S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylcarbamate (Compound III-12) 15.8 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 7.4 g, (yield 75%).

후처리

  1. washwashed with water (150 ml×3)
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel with PE

출처 및 근거

ORD 기록
ord-f3654a3c3ba0446e815cab133ae09437
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193734B2

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