Benzaldehyde → (R)-2-(Benzylamino)-3-hydroxypropanoic acid

HRID 1364100Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 71077D-Serine

Product 1

HCID 13543366(R)-2-(Benzylamino)-3-hydroxypropanoic acid

Procedure

The title compound was prepared from D-serine and benzaldehyde according to Method W and was obtained as a white solid (88%) that was used crude. δH (DMSO-d6) 7.45-7.30 (5H, m), 4.04-3.91 (2H, m), 3.70-3.61 (3H, m), 3.17 (1H, t, J 5.8 Hz). Not all exchangeable protons were observed.

Sources & evidence

ORD record: ord-fd68142d433244f3a2405f59c4489286
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888344B2

Reaction notes

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