Water → 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

HRID 1432020ノート

反応式

HRID 1432020 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]#[CH:21])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:22]([C@@H:25]([C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1)[CH3:26])=[N+:23]=[N-:24].[Na].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.O>O1CCOCC1.C(O)(C)(C)C>[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]([C:27]3[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=3)[CH3:26])[CH:21]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

7

反応物 4

HCID 962WaterHCID 16108955Methyl 4-[(1R)-1-azidoethyl]benzoateHCID 86604867(R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-oneHCID 178519209sodium (L)-ascorbate

生成物 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

試薬・触媒・溶媒 2

HCID 6386tert-Butanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of (R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydro-pyrazin-2(1H)-one (1.46 g, 4.24 mmol) and (R)-methyl 4-(1-azidoethyl)benzoate (0.870 g, 4.24 mmol) in dioxane (80 mL) and tert-butanol (120 mL) were added CuSO4.5H2O (1.11 g, 4.46 mmol in 8.0 mL H2O) and sodium-L-ascorbate (0.880 g, 4.44 mmol in 8.0 mL H2O). After 5 min, H2O (40 mL) was added and the reaction mixture was stirred for 16 h. The solvent was concentrated to approximately 40 mL under reduced pressure and diluted with 200 mL EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (1×100 mL). The extracts were washed with 5% NaHCO3 (200 mL×2), brine (200 mL×2), dried over Na2SO4 and concentrated under reduced pressure. The crude product was chromatographed on silica (100% CH2Cl2 to 10% MeOH in CH2Cl2) to yield the title compound.

後処理

  1. concentrationThe solvent was concentrated to approximately 40 mL under reduced pressure
  2. additiondiluted with 200 mL EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (1×100 mL)
  5. washThe extracts were washed with 5% NaHCO3 (200 mL×2), brine (200 mL×2)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was chromatographed on silica (100% CH2Cl2 to 10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-df44dd01047548f687ca0d9be56e9c18
出典データセット
uspto-grants-2009_11
特許番号
US07612060B2

反応ノート

読み込み中…