Alpha-methyldopa → HCID 53997397, compound

HRID 1590030Notes

Reaction equation

[NH2:1][C:2]([CH3:15])([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[C:3]([OH:5])=[O:4].N([C:18](C)([CH2:22][C:23]1C=CC(O)=C(OC)C=1)[C:19](O)=O)N>>[NH2:1][C:2]([CH3:15])([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)[C:3]([O:5][CH2:19][CH2:18][CH2:22][CH3:23])=[O:4]

Participants

Reactant 2

HCID 4138Alpha-methyldopa

HCID 3019911HCID 3019911, compound

Product 1

HCID 53997397HCID 53997397, compoundYield 82%

Procedure

The procedure of Example 1 is repeated employing 2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic acid rather than 2-hydrazino-2-methyl-3-(4-hydroxy-3-methoxyphenyl)propionic acid. The (±)-butyl 2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionate is obtained in a yield of 82%. The product is recrystallized from acetonitrile (77% yield) to give pure ester: mp 121.5° C. to 122° C.; HPLC analysis (C-18 column, 280 nm, tR =14.5 min) showed >99% purity.

Sources & evidence

ORD record: ord-0f2237d3d164487ea81b8c27609ec6e9
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202260

Reaction notes

Loading…