Hydrogen Bromide → 3-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1670501Notes

Reaction equation

HRID 1670501 reaction equation
[Cl:1][C:2]1[CH:45]=[CH:44][C:5]([CH2:6][CH:7]2[N:12]3[C:13](=[O:39])[CH:14]([NH:28]C(=O)OCC4C=CC=CC=4)[CH2:15][N:16]([S:17]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])(=[O:19])=[O:18])[CH:11]3[CH2:10][N:9]([CH:40]([CH3:42])[CH3:41])[C:8]2=[O:43])=[CH:4][CH:3]=1.Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[NH2:28][CH:14]1[C:13](=[O:39])[N:12]2[CH:7]([CH2:6][C:5]3[CH:44]=[CH:45][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:8](=[O:43])[N:9]([CH:40]([CH3:41])[CH3:42])[CH2:10][CH:11]2[N:16]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])(=[O:19])=[O:18])[CH2:15]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 86761388Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

Product 1

HCID 591342523-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 79 mg of benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate in 2 ml of a 33% solution of HBr in glacial acetic acid is stirred for 2 h. The reaction solution is mixed with aqueous sodium carbonate solution and extracted with ethyl acetate. The organic phase is dried over magnesium carbonate and 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=558.07 (calculated monoisotopic); measured value (M+H)+: 559.10.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium carbonate
  3. concentrationconcentrated under reduced pressure
  4. 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-6df629f5d6994ab88a3b965328e64f3b
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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