Hydrochloric Acid → HCID 58080194, compound

HRID 731541Notes

Reaction equation

HRID 731541 reaction equation
[NH2:1][C@@H:2]([CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][C:4]([N:6]([CH3:8])[CH3:7])=O.CO.Cl>C1COCC1>[NH2:1][C@@H:2]([CH2:9][S:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:3][CH2:4][N:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 59803658(3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamide

Product 1

HCID 58080194HCID 58080194, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 1L (8.68 g, 36.5 mmol) in THF (200 mL) was treated with BH3-dimethylsulfide (18.2 mL, 182.5 mmol) at room temperature, stirred overnight, treated slowly with methanol (20 mL), followed by 2N HCl (50 mL), stirred overnight, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 5% 7N NH3/CH3OH in dichloromethane to give the desired product (4.50 g, 55%). MS (CI) m/e 224 (M+H)+.

Workup

  1. stirringstirred overnight
  2. concentrationconcentrated
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with 5% 7N NH3/CH3OH in dichloromethane

Sources & evidence

ORD record
ord-991bf97da32b4c229899f08f97064be6
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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