Methanol → 4-((R)-1-(4-(((R)-1-(3 4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetra-hydropyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzaldehyde

HRID 1432022Notes

Reaction equation

HRID 1432022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@@H:25]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=3)[CH3:26])[CH:24]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CO>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:21]=[N:22][N:23]([C@@H:25]([C:27]3[CH:28]=[CH:29][C:30]([CH:33]=[O:34])=[CH:31][CH:32]=3)[CH3:26])[CH:24]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 887MethanolHCID 57932459(R)-4-(3,4-Dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(hydroxymethyl)-phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

Product 1

HCID 579324524-((R)-1-(4-(((R)-1-(3 4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetra-hydropyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(3,4-dichlorobenzenesulfonyl)-3-((1-((R)-1-(4-(hydroxymethyl)-phenyl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one (0.461 g, 0.882 mmol) in CH2Cl2 (100 mL) was added MnO2 (1.92 g, 22.1 mmol). After 1.5 h, MeOH (20 mL) was added. After the reaction mixture had stirred for 15 min, it was filtered through Celite and the solid was washed with CH2Cl2/MeOH (10/1). The solvent was removed under reduced pressure and dried in vacuo to yield the title compound.

Workup

  1. filtrationit was filtered through Celite
  2. washthe solid was washed with CH2Cl2/MeOH (10/1)
  3. customThe solvent was removed under reduced pressure
  4. customdried in vacuo

Sources & evidence

ORD record
ord-21d8013b59324b2c9d9c71b5c0f48c0c
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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