2-Benzyloxycarbamoyl-4-methyl-pentanoic acid → 2-Hydroxycarbamoyl-4-methylpentanoic acid

HRID 1669547Notes

Reaction equation

HRID 1669547 reaction equation
C([O:8][NH:9][C:10]([CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])=[O:11])C1C=CC=CC=1>C(O)C>[OH:8][NH:9][C:10]([CH:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])=[O:11]

Participants

3

Reactant 1

HCID 104455592-Benzyloxycarbamoyl-4-methyl-pentanoic acid

Product 1

HCID 15622-Hydroxycarbamoyl-4-methylpentanoic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate (3c) (6.6 g, 24.7 mmol) was dissolved into 75 mL ethanol and the solution was degassed with nitrogen. To the solution was added 1.3 g (20% by weight) Pd/C (10% by weight, wet) and the reaction was degassed under hydrogen. After 16 hours, the mixture was filtered through celite and the ethanol was removed in vacuo to yield intermediate (3d) (4.3 g) as a pink oil. 1H NMR (DMSO) δ (ppm): 0.7 (m, 6H), 1.2-1.4 (m, 1H), 1.4-1.6 (m, 2H), 2.9 (t, 1H), 3.3 (quart, 1H), 8.9 (br s, 1H), 10.5 (br s, 1H).

Workup

  1. customthe solution was degassed with nitrogen
  2. additionTo the solution was added 1.3 g (20% by weight) Pd/C (10% by weight, wet)
  3. customthe reaction was degassed under hydrogen
  4. filtrationthe mixture was filtered through celite
  5. customthe ethanol was removed in vacuo

Sources & evidence

ORD record
ord-56689b5bbbc74a42a1c0d4982f9bfa20
Source dataset
uspto-grants-2011_08
Patent number
US07989484B2

Reaction notes

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