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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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1-{[4-(4-Bromobenzenesulfonyloxy)-1-(2-tert-butoxycarbonylamino-3,3-dimethylbutyryl)-pyrrolidine-2-carbonyl]amino}-2-ethylcyclopropanecarboxylic acid methyl ester → 1-{[1-[2-(Bicyclo[3.1.0]hex-3-yloxycarbonylamino)-3,3-dimethyl-butyryl]-4-(4-bromobenzenesulfonyloxy)pyrrolidine-2-carbonyl]amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester

HRID 2405848
ノート
印刷プレビュー

反応式

HRID 2405848 の反応式
[CH3:1][O:2][C:3]([C:5]1([NH:10][C:11]([CH:13]2[CH2:17][CH:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][N:14]2[C:29](=[O:43])[CH:30]([NH:35][C:36]([O:38][C:39]([CH3:42])(C)[CH3:40])=[O:37])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:12])[CH2:7][CH:6]1[CH2:8][CH3:9])=[O:4].O=C1CCC(=O)N1OC(=O)OC1C[CH:58]2[CH:56]([CH2:57]2)C1>Cl.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1([NH:10][C:11]([CH:13]2[CH2:17][CH:16]([O:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][N:14]2[C:29](=[O:43])[CH:30]([NH:35][C:36]([O:38][CH:39]2[CH2:40][CH:58]3[CH:56]([CH2:57]3)[CH2:42]2)=[O:37])[C:31]([CH3:33])([CH3:32])[CH3:34])=[O:12])[CH2:7][CH:6]1[CH2:8][CH3:9])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 766049171-{[4-(4-Bromobenzenesulfonyloxy)-1-(2-tert-butoxycarbonylamino-3,3-dimethylbutyryl)-pyrrolidine-2-carbonyl]amino}-2-ethylcyclopropanecarboxylic acid methyl esterHCID 76604972Carbonic acid bicyclo[3.1.0]hex-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester

生成物 1

HCID 766050501-{[1-[2-(Bicyclo[3.1.0]hex-3-yloxycarbonylamino)-3,3-dimethyl-butyryl]-4-(4-bromobenzenesulfonyloxy)pyrrolidine-2-carbonyl]amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester収率 92%

試薬・触媒・溶媒

2
HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

1-{[4-(4-Bromobenzenesulfonyloxy)-1-(2-tert-butoxycarbonylamino-3,3-dimethylbutyryl)-pyrrolidine-2-carbonyl]amino}-2-ethylcyclopropanecarboxylic acid methyl ester was dissolved in 4N HCl in dioxane (300 mL) at room temperature and stirred for 2 h. It was then concentrated under vacuum, and co-evaporated with dichloromethane (2×200 mL) to dryness. The residue was dissolved in EtOAc (600 mL) and sat'd aq. NaHCO3 (1 L). It was stirred vigorously. After 10 min, carbonic acid bicyclo[3.1.0]hex-3-yl ester 2,5-dioxo-pyrrolidin-1-yl ester (41.4 g, 173.1 mmol) was added in one portion. After the resulting mixture was stirred for another 30 min, the organic layer was collect and washed with brine (500 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel with ethyl acetate/hexane to afford 94.4 g (92% yield) of 1-{[1-[2-(bicyclo[3.1.0]hex-3-yloxycarbonylamino)-3,3-dimethylbutyryl]-4-(4-bromobenzenesulfonyloxy)-pyrrolidine-2-carbonyl]-amino}-2-ethylcyclopropanecarboxylic acid methyl ester.

後処理

  1. concentrationIt was then concentrated under vacuum
  2. dissolutionThe residue was dissolved in EtOAc (600 mL)
  3. stirringIt was stirred vigorously
  4. waitAfter 10 min
  5. stirringAfter the resulting mixture was stirred for another 30 min
  6. customthe organic layer was collect
  7. washwashed with brine (500 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography on silica gel with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-073c5c025f1d45f58abb3f6ff190ea92
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08809267B2

反応ノート

読み込み中…

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