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 928060노트

반응식

HRID 928060 반응식
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

참가 물질

4

반응물 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-carboxylate2회

생성물 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-carboxylate수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-b86f538c27c645b4858d5a001299372f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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