2,3-Dihydroxybutanedioic Acid → Ethyl phenylglycinate, D-

Reaction equation

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

Participants

Reactant 2

HCID 8752,3-Dihydroxybutanedioic Acid

HCID 409886Ethyl phenylglycinate, DL-

Product 1

HCID 6922658Ethyl phenylglycinate, D-

Procedure

Similarly to Example 18 but using ethyl DL-phenylglycinate (5.070 g., -- contains 0.05 mole methylene chloride i.e. 27.6 mmole) and (+)-tartaric acid (4.275 g., 28.5 mmole, 1.03 equiv.) in the filtrate from a previous resolution (Example 18, 50 ml. -- made up to volume with the first and then second washes), and giving ethyl D-phenylglycinate (+)-hemitartrate solvated with 1.0 mole methanol (8.049 g., 81%), [α]D23 - 46.7° (c 2.520, H2O).

Sources & evidence

ORD record: ord-633fb4bb4a164671b7a240809dae19dd
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976680

Reaction notes

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