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

HRID 1097044Notes

Reaction equation

HRID 1097044 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.CCN=C=N[CH2:72][CH2:73][CH2:74]N(C)C.Cl>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:72]([CH2:73][CH2:74][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-1c70c7a6ccf24cf08e8d0706fb6ea5d9
Source dataset
uspto-grants-2012_03
Patent number
US08138345B2

Reaction notes

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