Methyl chloroformate → methyl 7-{N-[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778407ノート

反応式

HRID 1778407 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12].Cl[C:33]([O:35][CH3:36])=[O:34].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)[C:33]([O:35][CH3:36])=[O:34])(=[O:12])=[O:13]

参加物

6

反応物 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66685486methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate2 回

生成物 1

HCID 66685495methyl 7-{N-[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (60% dispersion in oil, 0.043 g) in THF (10 mL) was added methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 7, 0.40 g). Once gas evolution had ceased, methyl chloroformate (0.102 mL) was added and the resultant mixture was stirred at room temperature for 2.5 hours. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was triturated with ether to give methyl 7-{N[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate (0.230 g) as a white powder.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-44d3ed9f12da43d19fd802dbc75d2e97
出典データセット
uspto-grants-2016_02
特許番号
US09266896B2

反応ノート

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