Diisopropylethylamine → Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 2366334Notes

Reaction equation

HRID 2366334 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19](CNCCCCC(O)=O)=[O:20])[CH2:13][CH2:12]1)=[O:9].[O:36]1[CH2:40][CH2:39][O:38][CH:37]1[C:41]1[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=1.C([N:51]([CH2:55][CH3:56])[CH:52](C)C)(C)C.[OH:57]N1C2N=CC=CC=2N=N1.Cl.CN(C)[CH2:70][CH2:71][CH2:72]N=C=NCC>C(Cl)Cl>[O:36]1[CH2:40][CH2:39][O:38][CH:37]1[C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:70]([CH2:71][CH2:72][CH2:56][CH2:55][N:51]([CH3:52])[C:19]([CH2:18][CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([O:10][C:8](=[O:9])[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:12][CH2:13]2)=[O:20])=[O:57])=[CH:43][CH:42]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111266244-(1,3-Dioxolan-2-yl)anilineHCID 667818015-({3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)pentanoic acid

Product 1

HCID 66771476Biphenyl-2-ylcarbamic Acid 1-(2-{[4-(4-(1,3-Dioxolan-2-yl)-phenylcarbamoyl)butyl]methylcarbamoyl}ethyl)piperidin-4-yl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-({3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]-propionyl}methylamino)pentanoic acid (2.33 g, 4.84 mmol), 4-(1,3-dioxolan-2-yl)phenylamine (800 mg, 5 mmol) and N,N-diisopropylethylamine (1.26 mL, 7.26 mmol) in DCM (48.4 mL) was added 1-hydroxy-7-azabenzotriazole (692 mg, 5.08 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.39 g, 7.26 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (3.04 g, 100% yield) as a yellow solid.

Workup

  1. washThe reaction mixture was then washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50ebc96599f44be380cedaa7d6a5f70d
Source dataset
uspto-grants-2014_04
Patent number
US08697724B2

Reaction notes

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