Phenethylamine → (2S,3S)-3-Amino-2-hydroxy-N-phenethylpentanamide

Reaction equation

[NH2:1][C@@H:2]([CH2:11][CH3:12])[C@H:3]([OH:10])[C:4](NC1CC1)=[O:5].[C:13]1([CH2:19][CH2:20][NH2:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[NH2:1][C@@H:2]([CH2:11][CH3:12])[C@H:3]([OH:10])[C:4]([NH:21][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

Reactant 2

HCID 1001Phenethylamine

HCID 57872123(2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide

Product 1

HCID 86762428(2S,3S)-3-Amino-2-hydroxy-N-phenethylpentanamide

Procedure

The title compound was prepared in analogy to (2S,3S)-3-amino-N-cyclopropyl-2-hydroxypentanamide, Representative Procedure B, using 2-phenylethanamine in the seventh step (step B7).

Sources & evidence

ORD record: ord-714392896a3b40539122c9bc5fcfdc60
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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