2-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester → 2-Benzyloxycarbamoyl-4-methyl-pentanoic acid

HRID 1669546Notes

Reaction equation

HRID 1669546 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([C:10](=[O:20])[NH:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])C>[OH-].[Na+]>[CH2:13]([O:12][NH:11][C:10]([CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:21])=[O:3])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 104021382-Benzyloxycarbamoyl-4-methylpentanoic acid ethyl ester

Product 1

HCID 104455592-Benzyloxycarbamoyl-4-methyl-pentanoic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Intermediate (3b) (7.5 g, 25.5 mmol, 1.0 eq) was dissolved into 80 mL of 1N NaOH solution and stirred at room temperature overnight. The solution was then washed with 80 mL EtOAc, acidified to pH 1 with 6N HCl and extracted 2×100 mL EtOAc. The organic was dried over MgSO4 and concentrated to yield intermediate (3c) (6.6 g). 1H NMR (DMSO) δ (ppm): 1.0 (m, 6H), 1.4-1.8 (m, 3H), 1.3 (t, 3H), 1.5-1.7 (m, 1H), 3.2 (t, 1H), 4.9 (s, 2H), 7.4-7.6 (m, 5H) 11.4 (s, 1H).

Workup

  1. washThe solution was then washed with 80 mL EtOAc
  2. extractionextracted 2×100 mL EtOAc
  3. dry with materialThe organic was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-caa136743f7d40baa059238eb8416482
Source dataset
uspto-grants-2011_08
Patent number
US07989484B2

Reaction notes

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