D-Tartaric acid → Isofagomine D-(-)-Tartrate

HRID 251527Notes

Reaction equation

HRID 251527 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH2:11]1[NH:16][CH2:15][C@@H:14]([OH:17])[C@H:13]([OH:18])[C@H:12]1[CH2:19][OH:20]>O>[CH2:11]1[NH:16][CH2:15][C@@H:14]([OH:17])[C@H:13]([OH:18])[C@H:12]1[CH2:19][OH:20].[C:6]([C@H:4]([C@@H:2]([C:1]([O-:10])=[O:9])[OH:3])[OH:5])([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 447607Afegostat

Product 1

HCID 86616727Isofagomine D-(-)-TartrateYield 143.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of D-(−)-tartaric acid (102 mg, 0.679 mmol) in deionized water (1.0 mL) was added into the solution of isofagomine (200 mg, 2.0 equivalents) dissolved in deionized water (2.0 mL) at room temperature. The solution was stirred for 10 min and lyophilized overnight. The residue was further dried under vacuum at 45° C. for three days to afford the desired salt (287.2 mg, 95%). m.p. 94-95° C., 1H NMR (300 MHz, D2O): δ 4.22 (s, 2H), 3.71 (dd, J=12, 3.6 Hz, 1H), 3.67-3.59 (m, 2H), 3.44-3.36 (m, 3H), 2.85 (t, J=12 Hz, 1H), 2.75 (t, J=12 Hz, 1H), 1.84 (m, 1H) (FIG. 8B).

Workup

  1. waitlyophilized overnight
  2. customThe residue was further dried under vacuum at 45° C. for three days

Sources & evidence

ORD record
ord-77b5adfbcb8344a28555800b9135bc74
Source dataset
uspto-grants-2011_01
Patent number
US07863453B2

Reaction notes

Loading…