HCID 59803608, compound → (3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamide

HRID 731540Notes

Reaction equation

HRID 731540 reaction equation
[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]

Participants

3

Reactant 1

HCID 59803608HCID 59803608, compound

Product 1

HCID 59803658(3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A suspension of EXAMPLE 1K (10.60 g, 28.46 mmol) 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 (6.54 g, 96%). MS (CI) m/e 239 (M+H)+.

Workup

  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

Sources & evidence

ORD record
ord-d4df5dca14bf4549bca45a8d436a1a8b
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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