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Ammonium Chloride → (R)-3-(2-aminophenylthio)-2-(benzyloxycarbonylamino)-3-methylbutanoic acid

HRID 1055416
ノート
印刷プレビュー

反応式

HRID 1055416 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:16]([CH3:28])([S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-])=O)[CH3:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.[Zn]>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][C:16]([CH3:28])([CH3:17])[C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[C:13]([OH:15])=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 90037688(R)-2-(benzyloxycarbonylamino)-3-methyl-3-(2-nitrophenylthio)butanoic acid

生成物 1

HCID 90037504(R)-3-(2-aminophenylthio)-2-(benzyloxycarbonylamino)-3-methylbutanoic acid収率 100%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

A mixture of (R)-2-(benzyloxycarbonylamino)-3-methyl-3-(2-nitrophenylthio)butanoic acid (18.3 g, 45.2 mmol, Eq: 1.00), NH4Cl (4.84 g, 90.5 mmol, Eq: 2) and Zn (45.9 g, 701 mmol, Eq: 15.5) in MeOH (500 mL) was heated at reflux for 6 h and the mixture was filtered through Celite. The filter cake was washed with hot MeOH. The filtrate was concentrated, the residue was tritrurated with H2O, 1:3 Et2O/Hexane and azeotroped with toluene. The resulting material was dried under vacuum to give (R)-3-(2-aminophenylthio)-2-(benzyloxycarbonylamino)-3-methylbutanoic acid (16.9 g, 100%) which was used without purification.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. filtrationthe mixture was filtered through Celite
  4. washThe filter cake was washed with hot MeOH
  5. concentrationThe filtrate was concentrated
  6. customazeotroped with toluene
  7. customThe resulting material was dried under vacuum

出典と根拠

ORDレコード
ord-91a34fe137ee4ca89fc36a06108ab97a
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394263B2

反応ノート

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