Hydrochloric Acid → HCID 22949370, compound

HRID 1701046Notes

Reaction equation

HRID 1701046 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[N:11]=[C:10]([CH:12]([NH:24][CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[O:9][N:8]=1)=[O:6])[CH3:3].Cl.[CH3:27]C(O)C>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH3:3][CH:2]([O:4][C:5]([C:7]1[N:11]=[C:10]([CH:12]([NH:24][CH3:25])[CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[O:9][N:8]=1)=[O:6])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 70293055HCID 70293055, compound

Product 1

HCID 22949370HCID 22949370, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

5-(1-methylamino-2-(2-naphthyl)ethyl)-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester hydrochloride (1.64 g, 4.5 mmol) was suspended in 2-propanol (35 ml). After addition of tetraisopropyl titanate (1.3 g, 4.5 mmol) the reaction mixture was refluxed for 18 h. Hydrochloric acid (1N, 30 ml) was added and the reaction mixture was extracted with ethyl acetate (150 ml). The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (50 ml) and water (3×50 ml). After drying (magnesium sulfate) the solution was concentrated in vacuo to give 1.3 g of (R) 5-(1-methylamino-2-(2-naphthyl)ethyl)-[1,2,4]oxadiazole-3-carboxylic acid (2-propyl)ester that was used for the next step without further purification.

Workup

  1. temperaturewas refluxed for 18 h
  2. extractionthe reaction mixture was extracted with ethyl acetate (150 ml)
  3. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (50 ml) and water (3×50 ml)
  4. dry with materialAfter drying (magnesium sulfate) the solution
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-4ebb10db876b4c2b9835dd0b415c5c65
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

Loading…