Potassium Carbonate → Di-tert-butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)piperazine-1,3-dicarboxylate

HRID 493703Notes

Reaction equation

HRID 493703 reaction equation
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH2:5][NH:4][CH:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]1.[Cl:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([S:32]([CH2:35][CH2:36][C:37](O)=[O:38])(=[O:34])=[O:33])[CH:26]=[CH:25]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:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[C:27]([S:32]([CH2:35][CH2:36][C:37]([N:4]1[CH2:5][CH2:6][N:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][CH:3]1[C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])=[O:38])(=[O:33])=[O:34])[CH:26]=[CH:25]2

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2756817n-4-Boc-2-piperazinecarboxylic acid tert-butyl esterHCID 111973043-(6-Chloro-2-naphthyl)sulfonylpropionic acid

Product 1

HCID 23130894Di-tert-butyl 4-(3-((6-chloro-2-naphthyl)sulfonyl)propanoyl)piperazine-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Di-tert-butyl piperazine-1,3-dicarboxylate (Wu, Guosheng, et al., Enantiomer 6, pp. 343-345, (2001): 4.1 g) was dissolved in dichloromethane (50 mL), and triethylamine (4.0 mL) was added thereto. With ice cooling, 3-((6-chloro-2-naphthyl)sulfonyl)propionic acid (4.3 g), HOBt (2.4 g) and WSC (3.0 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, and the residue was purified with a silica gel column to give the title compound (5.0 g).

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
  5. customthe residue was purified with a silica gel column

Sources & evidence

ORD record
ord-5dce0c01f2eb4185aa74fe7ad76ceea6
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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