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 1432018ノート

反応式

HRID 1432018 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-eb347c17611b4a3c98607723e264e8c0
出典データセット
uspto-grants-2009_11
特許番号
US07612060B2

反応ノート

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