3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide → 6-(4-Chlorobenzyl)-8-isopropyl-1-(4-methoxybenzenesulfonyl)hexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 133087Notes

Reaction equation

HRID 133087 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:24][C:25](=[O:40])[CH2:26][CH2:27][NH:28][S:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:10]([N:12]([CH2:16][CH:17](OCC)OCC)[CH:13]([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1>C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]2[N:24]3[C:25](=[O:40])[CH2:26][CH2:27][N:28]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[CH:17]3[CH2:16][N:12]([CH:13]([CH3:14])[CH3:15])[C:10]2=[O:11])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 684528403-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide

Product 1

HCID 597352076-(4-Chlorobenzyl)-8-isopropyl-1-(4-methoxybenzenesulfonyl)hexahydropyrazino[1,2-a]pyrimidine-4,7-dione

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 167 mg of 3-(4-chlorophenyl)-N-(2,2-diethoxyethyl)-N-isopropyl-2-[3-(4-methoxybenzenesulfonylamino)propionylamino]propionamide in 3 ml of formic acid is stirred at room temperature for 12 h. The reaction solution is concentrated under reduced pressure, and the residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=506.02 (calculated); measured value (M+H)+: 506.34

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Sources & evidence

ORD record
ord-8826de113aa04c4c8a3467c0b3cc6fb6
Source dataset
uspto-grants-2008_06
Patent number
US07390814B2

Reaction notes

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