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

HRID 644337Notes

Reaction equation

HRID 644337 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].[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:31][CH2:30][C:29]3[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=3[NH:27][C:26]2=[O:36])[CH2:21][CH2:20]1.C1C[O:40][CH2:39]C1>>[O:36]=[C:26]1[N:25]([CH:22]2[CH2:21][CH2:20][N:19]([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])[CH2:24][CH2:23]2)[CH2:31][CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=2[NH:27]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 69720392ethyl (R)-2-amino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate

Product 1

HCID 69726684ethyl (R)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate

Procedure

A mixture of 20 mL THF, 1.65 g (6.7 mmol) ethyl (R)-2-amino-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propionate and 1.25 g (7.6 mmol) CDT was stirred for 1 h in the ice bath and for 1 h at RT. Then 1.70 g (6.9 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one was added and the mixture was refluxed for 3 h. The reaction mixture was evaporated down under reduced pressure, the residue 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-a5eef75612b34320a1a587157feebcdb
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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