Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate → Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

HRID 1994406Notes

Reaction equation

HRID 1994406 reaction equation
[CH2:1]([O:8][C:9](=[O:51])[NH:10][CH:11]([C:25](=[O:50])[NH:26][CH:27]([C:36](=[O:49])[N:37]([CH2:41][CH:42](OCC)OCC)[CH:38]([CH3:40])[CH3:39])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O>[CH2:1]([O:8][C:9](=[O:51])[NH:10][CH:11]1[C:25](=[O:50])[N:26]2[CH:27]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[C:36](=[O:49])[N:37]([CH:38]([CH3:40])[CH3:39])[CH2:41][CH:42]2[N:13]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])(=[O:16])=[O:15])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86761389Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

Product 1

HCID 86761388Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamateYield 92.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2.74 g (3.49 mmol) of benzyl[1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)-isopropylcarbamoyl]ethylcarbamoyl}-2-(2,4-dichlorobenzenesulfonylamino)ethyl]-carbamate in 45 ml of formic acid was heated at 60° C. for 6 h. The reaction mixture was then concentrated in vacuo, and the residue was purified by chromatography on 40 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM). 2.25 g of the cyclized compound are obtained as a colorless solid.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by chromatography on 40 g of SiO2 (eluent DCM followed by 20% EtOAc/DCM)

Sources & evidence

ORD record
ord-4400fd3ee7ca4968a97fd582810f4784
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

Loading…