(2S)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid → HCID 86722029、化合物

HRID 525009ノート

反応式

HRID 525009 の反応式
[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

参加物

3

反応物 2

HCID 7017896(2S)-3-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}propanoic acidHCID 70978853HCID 70978853、化合物

生成物 1

HCID 86722029HCID 86722029、化合物収率 26%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6649ebc1f9aa4b3bb0165495312224dc
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

反応ノート

読み込み中…