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Ethyl Acetate → 2-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester

HRID 899047
ノート
印刷プレビュー

反応式

HRID 899047 の反応式
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]([NH:15][CH:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]([NH:19][CH:20]([P:24](=[O:27])([OH:26])[OH:25])[CH:21]([CH3:23])[CH3:22])=[O:18])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:35][O:36][C:37](=[O:51])[CH:38](O)[CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C(OCC)(=O)C>CN(C=O)C>[CH3:35][O:36][C:37](=[O:51])[CH:38]([O:27][P:24]([CH:20]([NH:19][C:17](=[O:18])[CH:16]([NH:15][C:13]([O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:14])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH:21]([CH3:22])[CH3:23])([OH:26])=[O:25])[CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 543300255-Tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl esterHCID 54345348[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-phosphonic acid

生成物 1

HCID 570512352-{[1-(2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester
収率 66.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-5 °C

実験手順

Thionyl chloride (49 μL, 0.67 mmol) was added dropwise to a solution of [1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-phosphonic acid (208 mg, 0.48 mmol) in DMF (5 mL) at −20° C. under argon. The mixture was stirred for 35 min at −5° C. A solution of 5-tert-Butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester (166 mg, 0.67 mmol) in DMF (1 mL) was added and the mixture was stirred for 90 min at room temperature. Ethyl acetate was added and the mixture was washed with 1 M HCl, dried and concentrated under reduced pressure. The crude product was purified using chromathography (CHCl3/MeOH/H2O, 10:1:0→10:5:1) to give 2-{[1-(2-benzyloxycarbonylamino-3-phenyl-propionylamino)-2-methyl-propyl]-hydroxy-phosphinoyloxy}-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (211 mg, 66%).

後処理

  1. stirringthe mixture was stirred for 90 min at room temperature
  2. washthe mixture was washed with 1 M HCl
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified

出典と根拠

ORDレコード
ord-1de94f9dd14241c49dc2f9fc7823b52f
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354895B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート