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

HRID 1476268노트

반응식

HRID 1476268 반응식
[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]

참가 물질

4

반응물 1

HCID 59803608Benzyl [(R)-4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-YL]carbamate2회

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 260Hydrogen Bromide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2c0ce910cdc8403489d825b71957ec80
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018381B2

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