Tetrahydrofuran → (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)-propionic acid

HRID 644338Notes

Reaction equation

HRID 644338 reaction equation
C1COCC1.[O:6]=[C:7]1[N:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([NH:22][C@H:23]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=4[CH:31]=3)[C:24]([O:26]CC)=[O:25])=[O:21])[CH2:16][CH2:15]2)[CH2:12][CH2:11][C:10]2[CH:40]=[CH:41][CH:42]=[CH:43][C:9]=2[NH:8]1.O.[OH-].[Li+]>O>[O:6]=[C:7]1[N:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([NH:22][C@H:23]([CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=4[CH:31]=3)[C:24]([OH:26])=[O:25])=[O:21])[CH2:16][CH2:15]2)[CH2:12][CH2:11][C:10]2[CH:40]=[CH:41][CH:42]=[CH:43][C:9]=2[NH:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 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

Product 1

HCID 68578837(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)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 mL THF and 3.4 g (6.5 mmol) 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 was combined with a solution of 0.58 g (13.5 mmol) lithium hydroxide hydrate in 5 mL water and stirred overnight. The reaction mixture was evaporated down under reduced pressure, the residue was taken up in water and acidified by the addition of 1 M HCl. The precipitate was suction filtered and dried.

Workup

  1. customThe reaction mixture was evaporated down under reduced pressure
  2. additionacidified by the addition of 1 M HCl
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-16e951730e5b4837ba4a7ce785db8a70
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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