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Methyl iodide → (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

HRID 1650858
ノート
印刷プレビュー

反応式

HRID 1650858 の反応式
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])=[O:12])[CH2:7]1)(=[O:4])=[O:3].[CH2:19](N(CC)CC)C.CI>CO.O1CCCC1>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([CH3:19])[C@H:8]([C:11]([N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])=[O:12])[CH2:7]1)(=[O:4])=[O:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 18639279(2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

生成物 1

HCID 15056169(2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
40 °C

実験手順

To a solution of (2S,4R)-4-methanesulfonyloxy-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (14.9 g) in a mixture of methanol (150 ml) and tetrahydrofuran (150 ml) were added triethylamine (32.5 ml) and methyl iodide (11.4 ml) and the mixture was stirred at 40° C. for 2 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (600 g) eluting with a mixture of chloroform and methanol (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give a residue. The residue was washed with dichloromethane (100 ml). The resulting precipitates were collected and dried in vacuo to give (2S,4R)-4-methanesulfonyloxy-1-methyl-2-(2-oxoimidazolidin-1-yl)carbonylpyrrolidine (2.30 g).

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe resulting residue was chromatographed on silica gel (600 g)
  3. washeluting with a mixture of chloroform and methanol (9:1 V/V)
  4. additionThe fractions containing the desired compound
  5. customwere collected
  6. customevaporated in vacuo
  7. customto give a residue
  8. washThe residue was washed with dichloromethane (100 ml)
  9. customThe resulting precipitates
  10. customwere collected
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-3fe55ca3ddbf4134af3ec084ae6a5b0a
出典データセット
uspto-grants-1990_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04925838

反応ノート

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