Pyridine → methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927992노트

반응식

HRID 927992 반응식
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([CH:6]3[CH2:16][CH:7]3[CH2:8][O:9]2)=[CH:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1.N1C=CC=CC=1>C(Cl)Cl>[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:1][C:2]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]3[C:5]([CH:6]4[CH2:16][CH:7]4[CH2:8][O:9]3)=[CH:4][CH:3]=2)(=[O:26])=[O:25])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 27590464-Fluoro-2-nitrobenzene-1-sulfonyl chlorideHCID 86713293Methyl 5-amino-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 86713325methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate수율 57.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of methyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 42, 0.1 g), 4-fluoro-2-nitrobenzenesulfonyl chloride (0.115 g) and pyridine (2 mL) in DCM (5 mL) was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and filtered and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether (20%) to give methyl (1aRS,7bSR)-5-(4-fluoro-2-nitrobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.11 g) as a yellow oil.

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (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 ethyl acetate and petroleum ether (20%)

출처 및 근거

ORD 기록
ord-496fb99a84044b1e8924143a7f6243a2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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