Sodium Ascorbate → (R)-5-(4-(((R)-3-Oxo-1-(4-methylbenzenesulfonyl)-1,2,3,4-tetrahydropyrazin-2-yl)-methyl)-1H-1,2,3-triazol-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 1432018Notes

Reaction equation

HRID 1432018 reaction equation
[CH2:1]([C@H:4]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:8]=[CH:7][NH:6][C:5]1=[O:20])[C:2]#[CH:3].[N:21]([C@@H:24]1[CH2:33][CH2:32][CH2:31][C:30]2[CH:29]=[C:28]([CH:34]=[O:35])[CH:27]=[CH:26][C:25]1=2)=[N+:22]=[N-:23].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C>[O:20]=[C:5]1[NH:6][CH:7]=[CH:8][N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C@@H:4]1[CH2:1][C:2]1[N:23]=[N:22][N:21]([C@@H:24]2[CH2:33][CH2:32][CH2:31][C:30]3[CH:29]=[C:28]([CH:34]=[O:35])[CH:27]=[CH:26][C:25]2=3)[CH:3]=1

Participants

5

Reactant 3

HCID 23667548Sodium AscorbateHCID 59771822(R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehydeHCID 86604877(R)-3-(Prop-2-ynyl)-4-(4-methylbenzenesulfonyl)-3,4-dihydropyrazin-2(1H)-one

Product 1

HCID 57932484(R)-5-(4-(((R)-3-Oxo-1-(4-methylbenzenesulfonyl)-1,2,3,4-tetrahydropyrazin-2-yl)-methyl)-1H-1,2,3-triazol-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(R)-3-(Prop-2-ynyl)-4-(4-methylbenzenesulfonyl)-3,4-dihydropyrazin-2(1H)-one (2.5 mmol, 1.0 eq) and (R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde (2.5 mmol, 1 eq) were placed in t-BuOH to stir. An aqueous solution of sodium ascorbate (600 μL, 0.1 eq) was added, followed by the addition of an aqueous solution of CuSO4.5H2O (600 μL, 0.1 eq). The reaction mixture was allowed to stir overnight. The solvents were removed and the residue was purified by SiO2 (1 to 5% MeOH in DCM) to afford the title compound. MS (m/z): 492.4 (m+H).

Workup

  1. stirringto stir overnight
  2. customThe solvents were removed
  3. customthe residue was purified by SiO2 (1 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-eb347c17611b4a3c98607723e264e8c0
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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