Benzyl [(R)-4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-YL]carbamate → (3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamide

HRID 1771168ノート

反応式

HRID 1771168 の反応式
[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[CH2:4][C@@H:5]([NH:14]C(=O)OCC1C=CC=CC=1)[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>Br.C(O)(=O)C>[NH2:14][C@@H:5]([CH2:6][S:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][C:3]([N:2]([CH3:1])[CH3:26])=[O:25]

参加物

4

反応物 1

HCID 59803608Benzyl [(R)-4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-YL]carbamate2 回

生成物 1

HCID 59803658(3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamide収率 62.9%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 260Hydrogen Bromide溶媒

実験手順

A suspension of (R)-benzyl 4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-ylcarbamate (INTERMEDIATE 15, 40 g, 0.10 mol) in 40% HBr in acetic acid (100 ml) was stirred at room temperature for 16 hours and the reaction mixture became homogeneous during this time. The mixture was concentrated to dryness, diluted with water (200 ml) and AcOH (200 ml) and washed with diethyl ether (3×50 ml). The aqueous phase was brought to approximately pH 8-9 with solid Na2CO3 and was extracted with CH2Cl2 (5×) The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to give the title product (15 g, 59%) that was used in the preparation of INTERMEDIATE 17 without further purification.

後処理

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with water (200 ml) and AcOH (200 ml)
  3. washwashed with diethyl ether (3×50 ml)
  4. extractionwas extracted with CH2Cl2 (5×) The combined organic phases
  5. dry with materialwere dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ea67dccad91442f192d1f0ca7d905b23
出典データセット
uspto-grants-2016_02
特許番号
US09248140B2

反応ノート

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