Ammonium Acetate → HCID 13893049, compound

HRID 1744154Notes

Reaction equation

HRID 1744154 reaction equation
[N+](C1C=CC(C([O:10][C@@H:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=O)=CC=1)([O-])=O.C[O-].[Na+].C([O-])(=O)C.[NH4+]>CO>[OH:10][C@H:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 10942334Sodium MethoxideHCID 69153101HCID 69153101, compound

Product 1

HCID 13893049HCID 13893049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (1R)-1-(methoxycarbonyl)-3-methylbutyl 4-nitrobenzoate (1.59 g, 5.4 mmol) in methanol (15 mL) was added a freshly prepared solution of 1.5 M sodium methoxide in methanol (0.5 mL, 0.75 mmol). The resulting mixture was stirred at room temperature for 1 h, aqueous ammonium acetate (30 mL of 25% w/v) was added and the mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc in hexane to afford methyl (2R)-2-hydroxy-4-methylpentanoate as a colorless oil.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-56b4cde0870c4151afe36fe0adbfd734
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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