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

HRID 1750722ノート

反応式

HRID 1750722 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

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21893785Acetic Acid Mixture with Hydrobromic Acid溶媒

実験手順

A suspension of Example 1B (10.60 g) in 50 mL 30% HBr/acetic acid was stirred at room temperature overnight. The resulting homogeneous reaction mixture was concentrated, diluted with water (200 mL) and 5% HCl (100 mL), and washed with diethyl ether (3×). The aqueous phase was adjusted to pH 8-9 with solid Na2CO3 and extracted with dichloromethane (5×). The combined organic phases were dried (MgSO4), filtered, and concentrated to give the desired product.

後処理

  1. concentrationThe resulting homogeneous reaction mixture was concentrated
  2. additiondiluted with water (200 mL) and 5% HCl (100 mL)
  3. washwashed with diethyl ether (3×)
  4. extractionextracted with dichloromethane (5×)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-66a04742f8da4ac6b3b5caaaeba5f201
出典データセット
uspto-grants-2015_10
特許番号
US09156856B2

反応ノート

読み込み中…