p-Toluenesulfonic acid monohydrate → (R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

HRID 1432005ノート

反応式

HRID 1432005 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@H:13]([CH2:23][C:24]#[CH:25])[C:14]([NH:16][CH2:17][CH:18](OC)OC)=[O:15])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CC1C=CC(S(O)(=O)=O)=CC=1.O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:18]=[CH:17][NH:16][C:14](=[O:15])[C@H:13]2[CH2:23][C:24]#[CH:25])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86604868(R)-2-(3,4-dichlorobenzenesulfonamido)-N-(2,2-dimethoxyethyl)pent-4-ynamide

生成物 1

HCID 86604867(R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

A solution of (R)-2-(3,4-dichlorobenzenesulfonamido)-N-(2,2-dimethoxyethyl)pent-4-ynamide (36.7 g, 89.6 mmol) in 500 mL p-dioxane was treated with TsOH.H2O (5.11 g, 26.9 mmol). The reaction was heated to 60° C. for 7 h and then at 80° C. for 19 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with 400 mL EtOAc stirred with 400 mL 5% NaHCO3. The resulting precipitate was filtered and washed with H2O. The solid was suspended in hot EtOH and cooled to rt. The solid was collected by filtration, washed with EtOH and dried in vacuo to yield the title compound.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with 400 mL EtOAc
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with H2O
  6. temperaturecooled to rt
  7. filtrationThe solid was collected by filtration
  8. washwashed with EtOH
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-59642001d96a401590d92d9426a3b46d
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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