Methyl 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetrahydro-pyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzoate → (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

HRID 1432021ノート

反応式

HRID 1432021 の反応式
[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:36]=[CH:35][C:30]([C:31](OC)=[O:32])=[CH:29][CH:28]=3)[CH3:26])[CH:24]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]>C(Cl)Cl.C1(C)C=CC=CC=1>[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]([CH2:31][OH:32])=[CH:35][CH:36]=3)[CH3:26])[CH:24]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

4

反応物 1

HCID 57932491Methyl 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetrahydro-pyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzoate

生成物 1

HCID 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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

Methyl 4-((R)-1-(4-(((R)-1-(3,4-dichlorobenzenesulfonyl)-3-oxo-1,2,3,4-tetrahydro-pyrazin-2-yl)methyl)-1H-1,2,3-triazol-1-yl)ethyl)benzoate (1.38, 2.51 mmol) was dissolved in CH2Cl2 (200 mL) and cooled to −78° C. under N2. Dibal (1.5M solution in toluene, 8.4 mL, 12.6 mmol) was then added over 10 min. After 30 min, the cold bath was removed and the reaction was stirred for 4 h. To the solution was added MeOH (20 mL), followed by Na2SO4 (25.1 g) and saturated NH4Cl (2.5 mL). The reaction mixture was stirred overnight. The solids were removed by filtration, and washed with CH2Cl2/MeOH (10/1). The filtrate was concentrated and the residue was chromatographed on silica (100% CH2Cl2 to 5% MeOH in CH2Cl2) to yield the title compound.

後処理

  1. customthe cold bath was removed
  2. additionTo the solution was added MeOH (20 mL)
  3. stirringThe reaction mixture was stirred overnight
  4. customThe solids were removed by filtration
  5. washwashed with CH2Cl2/MeOH (10/1)
  6. concentrationThe filtrate was concentrated
  7. customthe residue was chromatographed on silica (100% CH2Cl2 to 5% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-82ed93cedeca4a1582214f565bf5a8b3
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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