Diethylamine → methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 927958노트

반응식

HRID 927958 반응식
CS(OS(C)(=O)=O)(=O)=O.[CH3:10][O:11][C:12]([N:14]([C:30]1[C:39]([C:40]([O:42][CH3:43])=[O:41])=[C:38]2[C:33]([CH:34]3[CH2:44][CH:35]3[CH2:36][O:37]2)=[CH:32][CH:31]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1/[CH:25]=[CH:26]\[CH2:27][CH2:28]O)(=[O:17])=[O:16])=[O:13].[CH:45]([N:48](C(C)C)[CH2:49][CH3:50])(C)[CH3:46].C(NCC)C>C(Cl)Cl.O>[CH3:10][O:11][C:12]([N:14]([C:30]1[C:39]([C:40]([O:42][CH3:43])=[O:41])=[C:38]2[C:33]([CH:34]3[CH2:44][CH:35]3[CH2:36][O:37]2)=[CH:32][CH:31]=1)[S:15]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1/[CH:25]=[CH:26]\[CH2:27][CH2:28][N:48]([CH2:49][CH3:50])[CH2:45][CH3:46])(=[O:17])=[O:16])=[O:13]

참가 물질

7

반응물 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 86713307Methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 90086604methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate수율 60.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Methyl sulfonic anhydride (0.062 g) was added to a stirred, cooled mixture of methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-4-hydroxybut-1-enyl)-4-fluorobenzene-sulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 73, 0.12 g) and N,N-di-isopropyl-N-ethylamine (0.046 g) in DCM (15 mL) at 0° C. The resultant mixture was stirred at 0° C. for 20 minutes. Diethylamine (0.026 g) was added and the mixture was then stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with DCM, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 2-10% to give methyl (1aRS,7bSR)-5-{N-(methoxycarbonyl)-N-[2((Z)-4-diethylaminobut-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.08 g) as alight yellow solid.

후처리

  1. temperaturecooled
  2. extractionextracted with DCM
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and DCM with a gradient of 2-10%

출처 및 근거

ORD 기록
ord-dfa2be822814449a8245921e9eb5ad85
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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