L-Tartaric acid → 2,3-Dihydroxybutanedioic Acid

HRID 1418119Notes

Reaction equation

HRID 1418119 reaction equation
[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][CH:10]1[C:13]([O:15][CH3:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>CO>[C:17]([OH:26])(=[O:25])[CH:18]([CH:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][CH:10]1[C:13]([O:15][CH3:16])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 15370446HCID 15370446, compound

Product 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 15370446HCID 15370446, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl N-[(S)-methylbenzyl]azetidine-2-carboxylate (0.27 g, the ratio: 2S isomer/2R isomer=52/48) and L-tartaric acid (0.15 g) were dissolved in methanol (6 ml) at room temperature. Then, the mixture was concentrated to give tartaric acid salt of methyl N-[(S)-methylbenzyl]azetidine-2-carboxylate, which was recrystallized from a mixed solvent of methyl tert-butyl ether (6 ml) and methanol (2 ml) to give crystals of tartaric acid salt of methyl N-[(S)-methylbenzyl]azetidine-2-(S)-carboxylate (0.12 g, colorless crystals, yield: 28%). 1H-NMR (DMSO), δ: 7.29 (m, 5 H); 4.39 (s, 2 H); 3.79 (t, J=8.3 Hz, 1 H); 3.70 (s, 3 H); 3.47 (q, J=6.3 Hz, 1 H); 3.00 (q, J=5.9 Hz, 1 H); 2.77 (q, J=7.6 Hz, 1 H); 2.18 (m, 2 H); 1.15 (d, J=6.3 Hz, 3 H).

Workup

  1. concentrationThen, the mixture was concentrated

Sources & evidence

ORD record
ord-1313342747f343cf91f477eea57e7e12
Source dataset
uspto-grants-1999_03
Patent number
US05880291

Reaction notes

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