Hydrochloric Acid → HCID 22949370, compound

HRID 849859Notes

Reaction equation

HRID 849859 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-f1247246e2424d81b3dcf706d4d0ab8d
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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