Methanol → 2,3-Dihydroxybutanedioic Acid

Participants

Reaction Steps

The free base (0.176 g, 0.1635 mmol) was dissolved in acetone (10 mL) and treated with one mole equivalent of L-tartaric acid in methanol (0.1M, 1.60 mL; 0.160 mmol). This mixture was concentrated and treated with dry ether and filtered to give 0.18 g of a tartaric acid salt of the the title compound; mp 150°-153° C.; IR (KBr) 3438, 3064, 2944, 1726, 1662, 1612, 1582, 1486 cm-1 ; MS (FAB) MH+ m/z 1071, (M+Na)+ m/z 1093, (M+K)+ m/z 1109; 1H-NMR (CDCl3) δ 1.112 (s, 2H), 1.218 (s, 3H), 1.705 (s, 3H), 1.804-2.116 (m, 6H), 2.221 (s, 3H), 2.373 (m, H), 2.441 (s, 3H), 2.545 (m, 3H), 3.454-3.697 (m, 4H), 3.794 (d, H), 4.170 (d, H), 4.320 (d, H), 4.445 (m, H), 4.951 (m, 2H), 5.671 (m, 2H), 6.026 (m, H), 6.250 (t, H), 6.287 (s, H), 7.098 (d, NH), 7.200-8.200 (m, 19H).

Provenance & Evidence