Acetic Acid → methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927990ノート

反応式

HRID 927990 の反応式
[CH3:1][O:2][C:3]([N:5]([C:19]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[N+:16]([O-])=O)(=[O:8])=[O:7])=[O:4].C(O)(=O)C>C(O)C.[Zn]>[CH3:1][O:2][C:3]([N:5]([C:19]1[C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[NH2:16])(=[O:7])=[O:8])=[O:4]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 86713324methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(4-fluoro-2-nitrobenzene-sulfonyl)amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate2 回

生成物 1

HCID 86713323methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate収率 80%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

実験手順

A mixture of methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(4-fluoro-2-nitrobenzene-sulfonyl)amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 111, 0.2 g), zinc (0.54 g) and acetic acid (0.5 g) in ethanol (20 mL) was stirred and heated at reflux for 1 hour. After cooling, the solid was filtered off and the filtrate was evaporated to dryness. The residue was treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50% to give methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.15 g) as a white solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered off
  5. customthe filtrate was evaporated to dryness
  6. additionThe residue was treated with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50%

出典と根拠

ORDレコード
ord-3274b17c794d4592ba07e9833e17a138
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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