Methanol → 2,3-Dihydroxybutanedioic Acid

HRID 2399184Notes

Reaction equation

HRID 2399184 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 (0.176 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).

Workup

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

Sources & evidence

ORD record
ord-1a4990b291924f47b7a7f55df1e028e5
Source dataset
uspto-grants-1995_09
Patent number
USH0001487

Reaction notes

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