Benzenepropanoic acid → N-(2-hydroxy-1-hydroxymethyl-ethyl)-3-phenyl-propionamide

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][CH:13]([CH2:16][OH:17])[CH2:14][OH:15]>>[OH:15][CH2:14][CH:13]([NH:12][C:9](=[O:11])[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:16][OH:17]

Participants

Reactant 2

HCID 107Benzenepropanoic acid

HCID 68294Serinol

Product 1

HCID 21260455N-(2-hydroxy-1-hydroxymethyl-ethyl)-3-phenyl-propionamide

Procedure

The procedure of example 79c was followed, using 3-phenylpropionic acid and serinol. At the end of the reaction, the DMF was evaporated and CH2Cl2 was added to the residue. The white crystalline material was collected and gave pure N-(2-hydroxy-1-hydroxymethyl-ethyl)-3-phenyl-propionamide as a white solid (56%, MS: m/e=224.2 (M+H+)).

Workup

customAt the end of the reaction
customthe DMF was evaporated
additionCH2Cl2 was added to the residue
customThe white crystalline material was collected

Sources & evidence

ORD record: ord-0816cec434254e5dbd036649f0c91b12
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184236B2

Reaction notes

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