L-Serine → HCID 66932750, compound

HRID 1364099Notes

Reaction equation

[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1>>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[CH:12][CH:11]=1

Participants

Reactant 2

HCID 5951L-Serine

HCID 312444-Methoxybenzaldehyde

Product 1

HCID 66932750HCID 66932750, compound

Procedure

The title compound was prepared from serine (29.6 g, 0.3 mmol) and p-methoxybenzaldehyde (68.0 mL, 0.6 mmol) according to Method W and was obtained as a white solid (36.2 g, 59%) that was used crude. δH (DMSO-d6) 7.37 (2H, dd, J 8.7 and 1.9 Hz), 6.93 (2H, dd, J 8.7 and 1.9 Hz), 3.99 (2H, s), 3.55 (3H, s), 3.73 (3H, m), 3.15 (1H, t, J 4.7 Hz). Not all exchangeable protons were observed.

Sources & evidence

ORD record: ord-ccbd7ce8fd6f4928bc376fd4963759e6
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888344B2

Reaction notes

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