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

HRID 2196744Notes

Reaction equation

HRID 2196744 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)butanamide

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

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.

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-aad26e754d70426d9d6658a7cf3f6aa5
Source dataset
uspto-grants-2012_12
Patent number
US08338466B2

Reaction notes

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