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 1432018노트

반응식

HRID 1432018 반응식
[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

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

(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).

후처리

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

출처 및 근거

ORD 기록
ord-eb347c17611b4a3c98607723e264e8c0
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612060B2

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