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

HRID 1784028Notes

Reaction equation

HRID 1784028 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 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of D-(−)-tartaric acid (204 mg, 1.359 mmol) in deionized water (2.0 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 (396.9 mg, 98%). m.p. 73-74° C., 1H NMR (300 MHz, D20): 6 4.41 (s, 2H), 3.71 (dd, J=12, 3.3 Hz, 1H), 3.66-3.59 (m, 2H), 3.44-3.36 (m, 3H), 2.84 (t, J=12 Hz, 1H), 2.75 (t, J=12 Hz, 1 H), 1.84 (m, 1H) (FIG. 8C)

Workup

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

Sources & evidence

ORD record
ord-907218e6526b4b39bc1c602a8542be49
Source dataset
uspto-grants-2009_03
Patent number
US07501439B2

Reaction notes

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