Sodium Hydroxide → 3-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

HRID 1080741Notes

Reaction equation

HRID 1080741 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][C:5]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:7])[CH3:6].[OH-].[Na+]>CO>[CH2:12]([O:11][C:9]([NH:8][C:5]([CH3:7])([CH3:6])[CH2:4][C:3]([OH:19])=[O:2])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15042554Methyl 3-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

Product 1

HCID 145510073-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 18.27 g (68.9 mmol) of 3-benzyloxycarbonylamino-3-methylbutanoic acid methyl ester in 20 mL of methanol at room temperature was treated dropwise with 51 mL of 2N NaOH (102 mmol). The mixture was stirred at room temperature for 16 hours then transferred to a separatory funnel and washed with hexane (3×). The aqueous layer was removed, cooled to 0° C. and slowly acidified to pH 2 (paper) by dropwise addition of 6N HCl. This mixture was extracted with ether (6×); combined extracts were washed with 1N HCl and brine, then dried over magnesium sulfate, filtered and solvent removed under vacuum to afford 17.26 g (68.7 mmol, 99%) of the product. 1H NMR (200 MHz, CDCl3): 1.42 (s, 6H), 2.77 (s, 2H), 5.06 (s, 2H), 5.2 (br s, 1H), 7.3 (s, 5H).

Workup

  1. customthen transferred to a separatory funnel
  2. washwashed with hexane (3×)
  3. customThe aqueous layer was removed
  4. temperaturecooled to 0° C.
  5. additionslowly acidified to pH 2 (paper) by dropwise addition of 6N HCl
  6. extractionThis mixture was extracted with ether (6×)
  7. washcombined extracts were washed with 1N HCl and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-8fa1cc43001f4a76a87ac7701abb178a
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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