Diisopropylcarbodiimide → HCID 11314837, compound

HRID 915615Notes

Reaction equation

HRID 915615 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[C:13]([C:14](O)=[O:15])[C:12]([OH:18])=[C:11]([I:19])[CH:10]=1.FC1C(O)=C(F)C(F)=C(F)C=1F.CC([N:35]=C=NC(C)C)C.C(=O)(O)[O-].[NH4+]>C(#N)C.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[C:13]([C:14]([NH2:35])=[O:15])[C:12]([OH:18])=[C:11]([I:19])[CH:10]=1

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 13041PentafluorophenolHCID 14013Ammonium BicarbonateHCID 43695632',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

Product 1

HCID 11314837HCID 11314837, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1 g (2.66 mmol) of 5-(2,4-difluorophenyl)-3-iodo-salicylic acid was mixed with 0.738 g (4.01 mmol) of pentafluorophenol in 20 ml of acetonitrile. 10 ml of N,N-diisopropylcarbodiimide was added at 0° C. and it was stirred continuously. 0.634 g of ammonium bicarbonate was dissolved in water. Consumption of the starting product was confirmed by HPLC and the crude was diluted with water and extracted with dichloromethane. The organic phase was dried over magnesium sulphate and purified on a silica gel column, using chloroform and methanol as eluents, in increasing polarity beginning with a proportion (v/v) of (40:1) up to (10:1).

Workup

  1. customConsumption of the starting product
  2. additionthe crude was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. custompurified on a silica gel column
  6. temperaturein increasing polarity beginning with a proportion (v/v) of (40:1) up to (10:1)

Sources & evidence

ORD record
ord-5f8f040d0e94423181a228c720a179ef
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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