Citric Acid → HCID 57624620, compound

HRID 1641568Notes

Reaction equation

HRID 1641568 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:28][C:29](=[O:31])[CH3:30])([CH2:23][O:24][C:25](=[O:27])[CH3:26])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:22])=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[CH3:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:25]([O:24][CH2:23][C:6]([NH:28][C:29](=[O:31])[CH3:30])([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:36]3[CH:37]=[CH:38][C:33]([CH3:32])=[CH:34][CH:35]=3)=[CH:17][C:16]=2[F:22])=[CH:11][CH:10]=1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 79799Tolylboronic acidHCID 46206782HCID 46206782, compound

Product 1

HCID 57624620HCID 57624620, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of N-[1,1-bis(acetoxymethyl)-3-(2′-fluoro-4′-hydroxybiphenyl-4-yl)propyl]acetamide (278 mg), 4-methylphenylboronic acid (175 mg), copper(II) acetate (117 mg), pyridine (255 mg) and molecular sieves 4A (500 mg) in methylene chloride (5 mL) was stirred at room temperature for 9 hr. 2% Aqueous citric acid solution (100 mL) was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (0.26 g) as white crystals.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2e533f70fdcb4ec6b23a8d5d1bb05572
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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