Hydrochloric Acid → HCID 58080194, compound

HRID 1750723Notes

Reaction equation

HRID 1750723 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>[CH3:8][N:6]([CH3:7])[CH2:4][CH2:3][C@@H:2]([NH2:1])[CH2:9][S:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

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

Product 1

HCID 58080194HCID 58080194, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 1C (8.68 g) in THF (200 mL) was treated with BH3-dimethylsulfide (18.2 mL) 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.

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-f2bd9599590d4486bbf27678f7a0cb43
Source dataset
uspto-grants-2015_10
Patent number
US09156856B2

Reaction notes

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