Reaction #77832

ord-f954d0b4badc4c8c9d0a3a32d1b865ff

Reaction equation

NS(=O)(=O)c1ccc(C(=O)N[C@H]2CCCC[C@H]2NC(=O)CNC(=O)OCc2ccccc2)cc1
benzyl (cis)-2-[(2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethylcarbamate
Br.CC(=O)O
HBr AcOH
CCOCC
Et2O
→
Br.NCC(=O)N[C@H]1CCCC[C@H]1NC(=O)c1ccc(S(N)(=O)=O)cc1
N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide

Reactants

NS(=O)(=O)c1ccc(C(=O)N[C@H]2CCCC[C@H]2NC(=O)CNC(=O)OCc2ccccc2)cc1
benzyl (cis)-2-[(2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethylcarbamate
Br.CC(=O)O
HBr AcOH
CCOCC
Et2O

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe solid was collected

Procedure

The material from above benzyl (cis)-2-[(2-{[4-(aminosulfonyl)benzoyl]amino}cyclohexyl)amino]-2-oxoethylcarbamate (217 mg) was dissolved in 30% HBr/AcOH (5 mL) at rt. After 1 h, Et2O was added and the solid was collected to give N-(cis)-{2-[(aminoacetyl)amino]cyclohexyl}-4-(aminosulfonyl)benzamide hydrogen bromide. MS found: (M+H)+=355.2.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706712B2uspto-grants-2004_03