Diethyl Ether → HCID 58959581, compound

HRID 133425Notes

Reaction equation

HRID 133425 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]([CH:22]([CH3:24])[CH3:23])[C:19]([OH:21])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(OCC)C.[N-:30]=[C:31]=[O:32].[O:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[CH:35]=[CH:34]1.C(N(CC)CC)C>C(Cl)Cl>[O:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[CH:35]=[C:34]1[NH:30][C:31]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:17][C@@H:18]([C:19]([OH:21])=[O:20])[CH:22]([CH3:24])[CH3:23])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1)=[O:32]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 67110068HCID 67110068, compoundHCID 86598633HCID 86598633, compound

Product 1

HCID 58959581HCID 58959581, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4′-Hydroxy-biphenyl-4-sulfonylamino)-3-methyl-butyric acid (314 mg, 0.9 mmol) dissolved in methylene chloride (10 mL) and diethyl ether (20 mL) was added with benzofuran isocyanate (143 mg, 0.9 mmol, 1 equiv) and triethyl amine (363 mg, 3.6 mmol, 4 equiv). The mixture was stirred at room temperature overnight. Solid precipitated from reaction mixture was collected by filtration followed by column chromatography (silica gel, 5% MeOH/CH2Cl2). 76 mg of white solid was obtained in 16% yield.

Workup

  1. customSolid precipitated from reaction mixture
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-6fd4553426154c0daf8f8355d094e298
Source dataset
uspto-grants-2008_06
Patent number
US07390833B2

Reaction notes

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