Piperidine-2-carboxylic acid tert-butylamide → 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide

HRID 1757735노트

반응식

HRID 1757735 반응식
[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:26]1[O:28][CH2:27]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:14]([O:21][C:22]([NH:24][C@@H:25]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:26]([OH:28])[CH2:27][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[C:6]([NH:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

4

반응물 2

HCID 5289197Piperidine-2-carboxylic acid tert-butylamideHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

생성물 1

HCID 569781971-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide수율 91.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2.576 g of N-tert.butyl-2(S)-piperidinecarboxamide and 4.158 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane in 70 ml of ethanol was heated at reflux for 16 hours. The solvent was removed by evaporation and the residue was dissolved in 100 ml of diethyl ether and treated with 10 g of activated magnesium silicate. The solvent was then removed by evaporation and there were obtained 6.16 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide as a colourless glass: MS: m/e 482 [M+H]+.

후처리

  1. temperatureat reflux for 16 hours
  2. customThe solvent was removed by evaporation
  3. dissolutionthe residue was dissolved in 100 ml of diethyl ether
  4. additiontreated with 10 g of activated magnesium silicate
  5. customThe solvent was then removed by evaporation

출처 및 근거

ORD 기록
ord-1fb0b742be5e416fb97065e287fec238
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05446161

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