4-Fluorophenol → HCID 12990921, compound

HRID 1827982Notes

Reaction equation

HRID 1827982 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11](=[O:33])[CH:12]([NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=1)=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:9][O:10][C:11](=[O:33])[CH:12]([NH:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:27][CH:26]=1)=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 69425655HCID 69425655, compound

Product 1

HCID 12990921HCID 12990921, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

p-Fluorophenol (75 mg, 0.7 mmol) was dissolved in DMSO along with 181 mg (0.5 mmol) 2-(4-chloromethylbenzyloxycarbonyl)amino-3-phenyl-propionic acid methyl ester 37. Cesium carbonate (300 mg) was added, and the suspension was stirred at room temperature for 2 hours. The reaction mixture was partitioned between ether and dilute aqueous HCl. The organic phase was dried, evaporated and chromatographed to give about 121 mg of 2-[4-(4-fluorophenoxy methyl) benzyloxycarbonylamino]-3-phenyl-propionic acid methyl ester 38.

Workup

  1. customThe reaction mixture was partitioned between ether and dilute aqueous HCl
  2. customThe organic phase was dried
  3. customevaporated
  4. customchromatographed

Sources & evidence

ORD record
ord-1ca56e4026e14136b352e2555fa33494
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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