HCID 57707105, compound → HCID 57705599, compound

HRID 1662582Notes

Reaction equation

HRID 1662582 reaction equation
CC1(C)OC(=O)[CH:5]([C:9]([CH3:26])([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)[CH2:10][CH3:11])[C:4](=[O:27])[O:3]1>CN(C=O)C.O.Cl>[CH3:26][C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1)([CH2:10][CH3:11])[CH2:5][C:4]([OH:27])=[O:3]

Participants

5

Reactant 1

HCID 57707105HCID 57707105, compound

Product 1

HCID 57705599HCID 57705599, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-(3-(benzyloxy)phenyl)butan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione 103.C (209 mg, 546 μmol) in DMF (2 mL) and H2O (0.2 mL) was heated to 90° C. overnight. The reaction was then diluted with 0.2N HCl, extracted with EtOAc, dried over MgSO4, filtered, stripped, and purified by silica gel chromatography to afford 3-(3-(benzyloxy)phenyl)-3-methylpentanoic acid 103.D (106.4 mg, 65.3% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-0c46e56b452849e39801b6d80c417b78
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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