2-Acetamido-3-(3,4-dihydroxyphenyl)prop-2-enoic acid → N-Acetyl-3-hydroxy-L-tyrosine

Reaction equation

[C:1]([NH:4][C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[H][H]>>[C:1]([NH:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 545313572-Acetamido-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

HCID 178418361HCID 178418361, compound

Product 1

HCID 13987867N-Acetyl-3-hydroxy-L-tyrosine

Procedure

reacting α-acetamido-3,4-dihydroxycinnamic acid with hydrogen in the presence of a catalytic amount of a chiral hyrogenation catalyst of the formula ##STR36## to produce N-acetyl-3,4-dihydroxy-L-phenylalanine; and (b) hydrolyzing the N-acetyl-3,4-dihydroxy-L-phenylalanine to produce 3,4-dihydroxy-L-phenylalanine.

Sources & evidence

ORD record: ord-6086fe7fc2fe49ab9b8293647f31bceb
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440936

Reaction notes

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