2-Dimethylaminopyridine → (+)-N-(t-butyloxy)-1-(4-methoxybenzenesulfonyl)-4-benzyloxycarbonyl-2-piperazinecarboxamide

HRID 343628Notes

Reaction equation

HRID 343628 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:14][CH:13]2[C:28](O)=[O:29])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[C:32]([O:36][NH2:37])([CH3:35])([CH3:34])[CH3:33].CN(C1C=CC=CN=1)C>C(Cl)Cl>[C:32]([O:36][NH:37][C:28]([CH:13]1[CH2:14][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:16][CH2:17][N:12]1[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])=[O:29])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 18675481HCID 18675481, compound

Product 1

HCID 18675468(+)-N-(t-butyloxy)-1-(4-methoxybenzenesulfonyl)-4-benzyloxycarbonyl-2-piperazinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-1-(4-methoxybenzenesulfonyl)-4-benzyloxycarbonyl-2-piperazinecarboxylic acid (100 mg, 0.23 mmol) in methylene chloride (5 ml) is added O-t-butylhydroxylamine hydrochloride (35 mg, 0.28 mmol), dimethylaminopyridine (37 mg, 0.30 mmol), and dicyclohexycarbodiimide (57 mg, 0.28 mmol). After stirring overnight, the reaction is diluted with hexanes and the precipitated solid filtered off. The solution is concentrated and the crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid) to provide (+)-N-(t-butyloxy)-1-(4-methoxybenzenesulfonyl)-4-benzyloxycarbonyl-2-piperazinecarboxamide.

Workup

  1. filtrationthe precipitated solid filtered off
  2. concentrationThe solution is concentrated
  3. customthe crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-885530eaa698446a99afbeef3fb546c1
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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