L-Tartaric acid → HCID 68882716, compound

HRID 1269493Notes

Reaction equation

HRID 1269493 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:19])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH:8]=1)[CH3:5].[C:21]([OH:30])(=[O:29])[C@@H:22]([C@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23]>C1COCC1>[C:26]([CH:24]([CH:22]([C:21]([OH:30])=[O:29])[OH:23])[OH:25])([OH:28])=[O:27].[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:5])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)[CH:8]=1)[CH3:19]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 68882717HCID 68882717, compound

Product 1

HCID 68882716HCID 68882716, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid methyl ester (4.80 g, 17.31 mmol) was dissolved in THF (80 mL) and followed by the addition of L-(+)-tartaric acid (2.86 g, 19.04 mmol). The resulting mixture was refluxed under nitrogen for 3 h. While the mixture was still hot, the solid was collected by vacuum-filtration, rinsed with THF, and further dried to afford 7.13 g (96%) of 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid methyl ester tartrate salt as a white solid: 1H NMR (DMSO-d6) δ 1.50 (s, 6H), 1.60–1.73 (m, 2H), 1.83 (d, 2H), 2.80–2.94 (m, 3H), 3.24 (d, 2H), 3.67 (s, 3H), 3.87 (s, 2H), 6.60 (d, 1H), 6.69 (s, 1H), 6.89 (d, 1H), 7.21 (t, 1H); MS m/z (relative intensity) 277 (M+, 2), 218 (6), 176 (100).

Workup

  1. temperatureThe resulting mixture was refluxed under nitrogen for 3 h
  2. filtrationthe solid was collected by vacuum-filtration
  3. washrinsed with THF
  4. customfurther dried

Sources & evidence

ORD record
ord-8c1c54be6b8c47269db43dd98962a609
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

Loading…