Potassium Carbonate → tert-Butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)-3-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 493708Notes

Reaction equation

HRID 493708 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[NH:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)[CH3:2].[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([S:31]([CH2:34][CH2:35][C:36](O)=[O:37])(=[O:33])=[O:32])[CH:25]=[CH:24]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(N(CC)CC)C>[Cl:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([S:31]([CH2:34][CH2:35][C:36]([N:11]1[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH:6]1[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:19])=[O:37])(=[O:32])=[O:33])[CH:25]=[CH:24]2

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 111973043-(6-Chloro-2-naphthyl)sulfonylpropionic acidHCID 16114865tert-Butyl 3-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylate

Product 1

HCID 23130960tert-Butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)-3-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylateYield 60.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

tert-Butyl 3-(2-ethoxy-2-oxoethyl)piperazine-1-carboxylate (0.9 g) was dissolved in dichloromethane (20 mL), and triethylamine (0.92 mL) was added thereto. With ice cooling, 3-((6-chloro-2-naphthyl)sulfonyl)propionic acid (1.0 g), HOBt (0.55 g) and WSC (0.65 g) were added thereto, and the mixture was mixed at room temperature for 16 hours. The reaction solution was basified with an aqueous potassium carbonate solution, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off to give the title compound (1.1 g) as a pale brown oily matter.

Workup

  1. additionthe mixture was mixed at room temperature for 16 hours
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-5ca0fc94541246eca32edbf048bd455c
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

Loading…