L-Tartaric acid → 2,3-Dihydroxybutanedioic Acid

HRID 2399182Notes

Reaction equation

HRID 2399182 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]>CC(C)=O>[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]

Participants

3

Reactant 1

HCID 444305L-Tartaric acid

Product 1

HCID 8752,3-Dihydroxybutanedioic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The free base was dissolved in acetone and treated with two mole equivalents of L-tartaric acid. This mixture was concentrated and treated with dry ether to give a tartaric acid salt of the title compound as a yellow solid; mp 170°-173° C.; IR (KBr) 3422, 3064, 2940, 2818, 1724, 1652, 1534 cm-1 ; MS (FAB) MH+ m/z 1100, (M+K)+ m/z 1138; 1H-NMR (CDCl3) δ 1.102 (s, 3H), 1.199 (s, 3H), 1.648 (s, 3H), 1.853 (m, H), 1.935 (s, 3H), 2.096 (m, H), 2.195 (s, 3H), 2.303 (m, H), 2.415 (s, 3H), 2.603-2.766 (m, 10H), 3.568 (S, 2H), 3.713 (m, 2H), 3.795 (d, H), 4.175 (d, H), 4.297 (d, H), 4.424 (m, H), 4.953 (d, H), 5.655 (m, 2H), 5.995 (m, H), 6.224 (t, H), 6.269 (S, H), 7.088 (d, NH), 7.200-8.200 (m, 19H).

Workup

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

Sources & evidence

ORD record
ord-cbec3e314c744264a55743201bfe3d95
Source dataset
uspto-grants-1995_09
Patent number
USH0001487

Reaction notes

Loading…