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Iodoethane → methyl (1aRS,7bSR)-5-[2-(1-ethylazetidin-3-yl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate

HRID 927971
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인쇄 미리보기

반응식

HRID 927971 반응식
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[S:12]([NH:15][C:16]2[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]3[C:19]([CH:20]4[CH2:30][CH:21]4[CH2:22][O:23]3)=[CH:18][CH:17]=2)(=[O:14])=[O:13])[CH2:2]1.I[CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:32]([N:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[S:12]([NH:15][C:16]2[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]3[C:19]([CH:20]4[CH2:30][CH:21]4[CH2:22][O:23]3)=[CH:18][CH:17]=2)(=[O:13])=[O:14])[CH2:2]1)[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 71006941methyl (1aRS,7bSR)-5-[2-(azetidin-3-yl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 77979733methyl (1aRS,7bSR)-5-[2-(1-ethylazetidin-3-yl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate수율 22.2%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

A mixture of methyl (1aRS,7bSR)-5-[2-(azetidin-3-yl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 87, 0.216 g), iodoethane (0.078 g) and potassium carbonate (0.138 g) in acetonitrile (5 mL) was stirred at room temperature for 18 hours. The mixture 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 0-15% to give methyl (1aRS,7bSR)-5-[2-(1-ethylazetidin-3-yl)-4-fluorobenzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.051 g).

후처리

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of methanol and DCM with a gradient of 0-15%

출처 및 근거

ORD 기록
ord-b94e7edc54df4b129bf2be585d886362
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290472B2

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