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

HRID 1033373Notes

Reaction equation

HRID 1033373 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([O:16]C)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:19])([CH3:18])[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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 methyl 3-benzyloxycarbonylamino-3-methylbutanoate (Step D) in 20 mL of methanol at room temperature was treated dropwise wit 51 mL of 2N NaOH (102 mmol, 1.5 eq). 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° 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,6 H), 2.77 (s,2 H), 5.06 (s,2 H), 5.2 (br s,1 H), 7.3 (s,5 H).

Workup

  1. customthen transferred to a separatory funnel
  2. washwashed with hexane (3×)
  3. customThe aqueous layer was removed
  4. temperaturecooled to 0°
  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-27fb14c00a0347f59aa0a6a7d13b7a64
Source dataset
uspto-grants-1994_05
Patent number
US05310737

Reaction notes

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