(2S)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid → HCID 86722029, 화합물

HRID 525009노트

반응식

HRID 525009 반응식
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([NH:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[O:9].[C:19]([O:23][CH2:24][C@H:25]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:26](O)=[O:27])([CH3:22])([CH3:21])[CH3:20]>>[Br:7][C:4]1[CH:5]=[CH:6][N:2]([NH:1][C:26](=[O:27])[C@@H:25]([NH:29][C:30](=[O:31])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:24][O:23][C:19]([CH3:22])([CH3:21])[CH3:20])[C:3]=1[C:8](=[O:9])[NH:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1

참가 물질

3

반응물 2

HCID 7017896(2S)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 70978853HCID 70978853, 화합물

생성물 1

HCID 86722029HCID 86722029, 화합물수율 26%

실험 절차

Prepared according to the experimental procedure described in Preparation 61a from 1.07 g (3.39 mmol) of 1-amino-3-bromo-N-(3,5-difluorophenyl)-1H-pyrrole-2-carboxamide and 1.65 g (3.73 mmol) of (S)-3-tert-butoxy-2-(tert-butoxycarbonylamino)propanoic acid. After stirring the reaction mixture overnight, an excess of an additional 1.65 g (3.73 mmol) of the acid was added and the reaction stirred for yet 24 hours more. After precipitation and filtration of the product, two purification steps were needed. First by flash chromatography (70% to 100% DCM/hexanes) and a second purification by reverse phase chromatography (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%). 494 mg (26% yield) of the title compound were isolated as a white solid.

후처리

  1. customPrepared
  2. stirringthe reaction stirred for yet 24 hours more
  3. customAfter precipitation and filtration of the product, two purification steps
  4. customFirst by flash chromatography (70% to 100% DCM/hexanes) and a second purification by reverse phase chromatography (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid

출처 및 근거

ORD 기록
ord-6649ebc1f9aa4b3bb0165495312224dc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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