Hydrochloric Acid → methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 928060ノート

反応式

HRID 928060 の反応式
Cl.[Si]([O:9][CH2:10]/[C:11](/[CH3:43])=[CH:12]\[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[S:20]([N:23]([C:28]1[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:36]2[C:31]([CH:32]3[CH2:42][CH:33]3[CH2:34][O:35]2)=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21])(C(C)(C)C)(C)C>CO>[F:19][C:17]1[CH:16]=[CH:15][C:14]([S:20]([N:23]([C:28]2[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:36]3[C:31]([CH:32]4[CH2:42][CH:33]4[CH2:34][O:35]3)=[CH:30][CH:29]=2)[C:24]([O:26][CH3:27])=[O:25])(=[O:22])=[O:21])=[C:13](/[CH:12]=[C:11](/[CH3:43])\[CH2:10][OH:9])[CH:18]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86713360methyl (1aRS,7bSR)-5-(N-{2-[(Z)-3-(tert-butyldimethylsilanyloxy)-2-methylprop-1-enyl]-4-fluorobenzenesulfonyl]-N-methoxycarbonyl-amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2 回

生成物 1

HCID 71007016methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Concentrated hydrochloric acid (1 mL) was added to a solution of methyl (1aRS,7bSR)-5-(N-{2[(Z)-3-(tert-butyldimethylsilanyloxy)-2-methylprop-1-enyl]-4-fluorobenzenesulfonyl]-N-methoxycarbonyl-amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 202, 0.385 g) in methanol (20 mL) and the mixture was left at room temperature for 45 minutes. The solution 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 0-60% to give methyl (1aRS,7bSR)-5-{N-[4-fluoro-2-((Z)-3-hydroxy-2-methylprop-1-enyl)benzenesulfonyl]-N-methoxycarbonylamino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.314 g) as a white foam.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

出典と根拠

ORDレコード
ord-b86f538c27c645b4858d5a001299372f
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

読み込み中…