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

HRID 1055416
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HRID 1055416 반응식
[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]
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반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91a34fe137ee4ca89fc36a06108ab97a
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394263B2

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