Tetrahydrofuran → ethyl (R)-2-{[4-(5-oxo-3-phenyl-4,5-dihydro-[1,2,4]triazol-1-yl)-piperidine-1-carbonyl]-amino}-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate

HRID 644344Notes

Reaction equation

HRID 644344 reaction equation
[NH2:1][C@H:2]([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:19]1([C:25]2[NH:26][C:27](=[O:36])[N:28]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[N:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C[O:40][CH2:39]C1>>[O:36]=[C:27]1[N:28]([CH:30]2[CH2:31][CH2:32][N:33]([C:39]([NH:1][C@H:2]([CH2:8][C:9]3[CH:18]=[CH:17][C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[CH:10]=3)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:40])[CH2:34][CH2:35]2)[N:29]=[C:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:26]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 69720392ethyl (R)-2-amino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionateHCID 1356275985-Phenyl-2-piperidin-4-YL-2,4-dihydro-[1,2,4]triazol-3-one

Product 1

HCID 136388296ethyl (R)-2-{[4-(5-oxo-3-phenyl-4,5-dihydro-[1,2,4]triazol-1-yl)-piperidine-1-carbonyl]-amino}-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate

Procedure

A mixture of 15 mL THF, 0.830 g (3.4 mmol) ethyl (R)-2-amino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate and 0.63 g (3.8 mmol) CDT was stirred for 1 h in the ice bath and for 1 h at RT. Then 0.83 g (3.4 mmol) 5-phenyl-2-piperidin-4-yl-2,4-dihydro-[1,2,4]triazol-3-one was added and the mixture was refluxed for 3 h. The reaction mixture was evaporated down under reduced pressure, the residue was combined with 15% K2CO3 solution, the precipitate was suction filtered and dried.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. customThe reaction mixture was evaporated down under reduced pressure
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-1f13717b011447658f30078d335eb336
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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