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

HRID 1784027Notes

Reaction equation

HRID 1784027 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, 1 H), 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-67b86b27891f4c62aced766825510af3
Source dataset
uspto-grants-2009_03
Patent number
US07501439B2

Reaction notes

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