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Ethylamine → methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate

HRID 927950
ノート
印刷プレビュー

反応式

HRID 927950 の反応式
CS(OS(C)(=O)=O)(=O)=O.COC([N:14]([C:29]1[C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]2[C:32]([CH:33]3[CH2:43][CH:34]3[CH2:35][O:36]2)=[CH:31][CH:30]=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]O)(=[O:17])=[O:16])=O.[CH:44]([N:47](C(C)C)CC)(C)[CH3:45].C(N)C>C(Cl)Cl.O>[CH2:44]([NH:47][CH2:27]/[CH:26]=[CH:25]\[C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[S:15]([NH:14][C:29]1[C:38]([C:39]([O:41][CH3:42])=[O:40])=[C:37]2[C:32]([CH:33]3[CH2:43][CH:34]3[CH2:35][O:36]2)=[CH:31][CH:30]=1)(=[O:17])=[O:16])[CH3:45]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 86713304methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2 回

生成物 1

HCID 86713248
methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate
収率 56.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Methane sulfonic anhydride (0.09 g) was added to a stirred, cooled mixture of methyl (1aRS,7bSR)-5-{N-[methoxycarbonyl]-N-[2-((Z)-3-hydroxyprop-1-enyl)-4-fluorobenzenesulfonyl]amino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 64, 0.17 g) and N,N-di-isopropyl-N-ethylamine (0.134 g) in DCM (10 mL) at 0° C. The temperature was allowed to rise to room temperature and the mixture was stirred for 2 hours. A solution of ethylamine (2M in toluene, 2 mL) was added and the resultant mixture was stirred at room temperature for 3 hours then diluted with water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give methyl (1aRS,7bSR)-5-[2((Z)-3-ethylaminoprop-1-enyl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (0.09 g) as a white solid.

後処理

  1. temperaturecooled
  2. customto rise to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-4452265775a647a19d57d5930e3510e8
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09290472B2

反応ノート

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