Triethylamine → 2-[4-(4-Acetoxypiperidin-1-carbonyl)benzyl]-3-isopropylmaleic acid dimethyl ester

HRID 418760Notes

Reaction equation

HRID 418760 reaction equation
[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[C:47]([O:50][CH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)(=[O:49])[CH3:48].C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:54]2[CH2:55][CH2:56][CH:51]([O:50][C:47](=[O:49])[CH3:48])[CH2:52][CH2:53]2)=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:11])[CH3:12])\[C:6]([O:8][CH3:9])=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12694334Piperidin-4-yl acetate hydrochlorideHCID 666486782-(4-Carboxybenzyl)-3-isopropylmaleic acid dimethyl ester

Product 1

HCID 597065112-[4-(4-Acetoxypiperidin-1-carbonyl)benzyl]-3-isopropylmaleic acid dimethyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-carboxybenzyl)-3-isopropylmaleic acid dimethyl ester (10.3 mg, 0.0322 mmol) in dichloromethane (500 μL) were added 1-hydroxybenzotriazole (13.3 mg, 0.0965 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20.8 mg, 0.109 mol), piperidin-4-yl acetate hydrochloride (28.8 mg, 0.161 mmol) and triethylamine (14.6 mg, 0.145 mmol) with stirring under ice cooling. After stirring at room temperature for 1 h, the reaction mixture was diluted with water to separate the phases. The aqueous layer was extracted again with ethyl acetate, and the combined organic layer was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate1:2) to give 11.1 mg of the title compound as a solid (yield: 78%).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. customto separate the phases
  3. extractionThe aqueous layer was extracted again with ethyl acetate
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-0220469dc0634d2ea3dafad27955edad
Source dataset
uspto-grants-2012_01
Patent number
US08093294B2

Reaction notes

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