Sodium Ascorbate → (R)-4-(3,4-dichlorophenylsulfonyl)-3-((1-((R)-2-(2,2,2-trifluoroacetyl)-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinolin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

HRID 1432027Notes

Reaction equation

HRID 1432027 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]#[CH:21])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:22]([C@H:25]1[C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][C:29]=2[CH2:28][CH2:27][CH2:26]1)[CH2:36][N:35]([C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])[CH2:34][CH2:33]3)=[N+:23]=[N-:24].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>O1CCOCC1.CC(O)(C)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[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:24]=[N:23][N:22]([C@H:25]3[C:30]4[CH:31]=[C:32]5[C:37](=[CH:38][C:29]=4[CH2:28][CH2:27][CH2:26]3)[CH2:36][N:35]([C:39](=[O:44])[C:40]([F:41])([F:43])[F:42])[CH2:34][CH2:33]5)[CH:21]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 3

HCID 23667548Sodium AscorbateHCID 58597252(R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanoneHCID 86604867(R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

Product 1

HCID 86760974(R)-4-(3,4-dichlorophenylsulfonyl)-3-((1-((R)-2-(2,2,2-trifluoroacetyl)-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinolin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

Reagents, catalysts & solvents 4

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-4-(3,4-dichlorophenylsulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one (345 mg, 1 mmol) and (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone (324 mg, 1 mmol) in dioxane (3 mL) and t-BuOH (4 mL) was added a solution of copper(2+) sulfate, pentahydrate (249 mg, 1 mmol) in water (0.5 mL), followed by a solution of (+)-sodium l-ascorbate (198 mg, 1 mmol) in water (0.5 mL). The resulting solution was stirred at room temperature for 16.

Sources & evidence

ORD record
ord-e6908732360f4122b80834c4759e348c
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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