Methanol → 2,3-Dihydroxybutanedioic Acid

HRID 2399183Notes

Reaction equation

HRID 2399183 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].CO>CC(C)=O>[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 444305L-Tartaric acid

Product 1

HCID 8752,3-Dihydroxybutanedioic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The free base (0.32 g; 0.2914 mmol) was dissolved in acetone (10 mL) and treated with 0.1M L-tartaric acid in MeOH (2.9 mL; 0.29 mmol). This mixture was concentrated and treated with dry ether to give a tartaric acid salt of the title compound as a white solid; mp 178°-180° C.; IR (KBr) 3440, 3064, 3030, 2934, 2802, 1662, 1610, 1582, 1518, 1486, 1452, 1372 cm-1 ; MS (FAB) MH+ m/z 1099, (M+Na)+ m/z 1121, (M+K)+ m/z 1137; 1H-NMR (CDCl3) δ 1.119 (s, 3H), 1.217 (s, 3H), 1.518 (m, 7H), 1.667 (s, 3H), 1.873 (m, H), 1.957 (s, 3H), 2.111 (m, H), 2.215 (s, 3H), 2.316 (m, H), 2.432 (s, 3H), 2.597 (m, H), 2.875 (m, 2H), 3.684 (m, 2H), 3.816 (d, H), 4.196 (d, H), 4.370 (d, H), 4.440 (m, H), 4.975 (d, H), 5.665 (m, 2H), 6.030 (m, H), 6.252 (t, H), 6.284 (S, H), 7.096 (d, NH), 7.200-8.700 (m, 19H) .

Workup

  1. concentrationThis mixture was concentrated
  2. additiontreated with dry ether

Sources & evidence

ORD record
ord-e2442e2e4b14470f8df6a9247aa6bafb
Source dataset
uspto-grants-1995_09
Patent number
USH0001487

Reaction notes

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