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

HRID 1476268Notes

Reaction equation

HRID 1476268 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

4

Reactant 1

HCID 59803608HCID 59803608, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2c0ce910cdc8403489d825b71957ec80
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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