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Dibenzyl ether → 4-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-6-hydroxy-hexanoyl]-piperazine-1-carboxylic acid butyl ester

HRID 1970614
ノート
印刷プレビュー

反応式

HRID 1970614 の反応式
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:58])[C@@H:15]([NH:28][C:29]([C:31]2[CH:35]=[C:34]([O:36][CH2:37][C:38]([N:40]3[CH2:44][CH2:43][CH2:42][C@H:41]3[C:45](=[O:51])[NH:46][CH:47]3[CH2:50][CH2:49][CH2:48]3)=[O:39])[N:33]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[N:32]=2)=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][O:20]CC2C=CC=CC=2)[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(OCC1C=CC=CC=1)C1C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:58])[C@@H:15]([NH:28][C:29]([C:31]2[CH:35]=[C:34]([O:36][CH2:37][C:38]([N:40]3[CH2:44][CH2:43][CH2:42][C@H:41]3[C:45](=[O:51])[NH:46][CH:47]3[CH2:48][CH2:49][CH2:50]3)=[O:39])[N:33]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[N:32]=2)=[O:30])[CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 7657Dibenzyl etherHCID 668571284-[(S)-6-Benzyloxy-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-hexanoyl]-piperazine-1-carboxylic acid butyl ester

生成物 1

HCID 668562204-[(S)-2-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-6-hydroxy-hexanoyl]-piperazine-1-carboxylic acid butyl ester収率 1.1%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

To a solution of 819 mg 4-[(S)-6-Benzyloxy-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-hexanoyl]-piperazine-1-carboxylic acid butyl ester in 20 ml ethyl acetate were added under argon 100 mg Pd/C (10%) and the suspension was stirred under an atmosphere of hydrogen (3 bar) for 12 h. The suspension was filtered over a plug of Celite® and washed with ethyl acetate. The crude product obtained after evaporation of the solvent was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA) to give a mixture of the title compound (8 mg) and unreacted benzyl ether which was subjected to the same hydrogenolysis conditions described above to give the title compound.

後処理

  1. filtrationThe suspension was filtered over a plug of Celite®
  2. washwashed with ethyl acetate
  3. customThe crude product obtained
  4. customafter evaporation of the solvent
  5. customwas purified by preparative HPLC (
  6. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  7. customto give

出典と根拠

ORDレコード
ord-2f9955f1299c417fa4b0f179a40cd6f3
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426420B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート