2-Methyl-5-phenylpentan-2-amine → Ethyl 3-(3-{(1S)-2-[(1,1-dimethyl-4-phenylbutyl)amino]-1-hydroxyethyl}-4,5-difluorophenyl)propanoate

HRID 602038Notes

Reaction equation

HRID 602038 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[C:6]([C@H:9]2[CH2:11][O:10]2)[C:7]=1[F:8].[CH3:19][C:20]([NH2:31])([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[CH3:30][C:20]([NH:31][CH2:11][C@H:9]([C:6]1[CH:5]=[C:4]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=[C:2]([F:1])[C:7]=1[F:8])[OH:10])([CH3:19])[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 122500142-Methyl-5-phenylpentan-2-amineHCID 57470574Ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}propanoate

Product 1

HCID 24957327Ethyl 3-(3-{(1S)-2-[(1,1-dimethyl-4-phenylbutyl)amino]-1-hydroxyethyl}-4,5-difluorophenyl)propanoateYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-{3,4-difluoro-5-[(2S)-2-oxiranyl]phenyl}propanoate (11.07 g, 43.2 mmol) and (1,1-dimethyl-4-phenylbutyl)amine (7.68 g, 43.4 mmol) in ethanol (50 mL) was heated at 70° C. for 36 h. The reaction was concentrated and purified by column chromatography (0-90% ethyl acetate:hexane) afforded the desired product (14.54 g, 78%). MS (m/z): 434.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (0-90% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-9604c7d34436482089b682d9b7be579a
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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