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Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate → methyl (1aRS,7bSR)-5-[4-fluoro-2-(methoxycarbonylmethyl)-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927969
ノート
印刷プレビュー

反応式

HRID 927969 の反応式
Cl[S:2]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:4])=[O:3].[NH2:17][C:18]1[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]2[C:21]([CH:22]3[CH2:32][CH:23]3[CH2:24][O:25]2)=[CH:20][CH:19]=1>N1C=CC=CC=1.C(Cl)Cl>[F:11][C:8]1[CH:9]=[CH:10][C:5]([S:2]([NH:17][C:18]2[C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]3[C:21]([CH:22]4[CH2:32][CH:23]4[CH2:24][O:25]3)=[CH:20][CH:19]=2)(=[O:4])=[O:3])=[C:6]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:7]=1
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 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2 回HCID 86713311Methyl (2-chlorosulfonyl-5-fluorophenyl)acetate2 回

生成物 1

HCID 71006868methyl (1aRS,7bSR)-5-[4-fluoro-2-(methoxycarbonylmethyl)-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate収率 97.6%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A solution of methyl (2-chlorosulfonyl-5-fluorophenyl)acetate (Intermediate 85, 0.293 g) and methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 42, 0.219 g) in pyridine (1 mL) and DCM (3 mL) was left to stand at room temperature for 4 days. The mixture was diluted with DCM, washed with 2M hydrochloric acid and filtered through a phase separator. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-40% to give methyl (1aRS,7bSR)-5-[4-fluoro-2-(methoxycarbonylmethyl)-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.438 g) as a colourless gum.

後処理

  1. washwashed with 2M hydrochloric acid
  2. filtrationfiltered through a phase separator
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica
  5. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-40%

出典と根拠

ORDレコード
ord-934e4b94cfd54d0787c96b2dae5bbcad
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290472B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート