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

HRID 1379862Notes

Reaction equation

HRID 1379862 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 18.3 g (68.9 mmol) of methyl 3-benzyloxycarbonylamino-3-methylbutanoate (Step B) in 20 mL of methanol at room temperature was treated dropwise with 51 mL of 2 N 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 6 N HCl. This mixture was extracted with ether (6×); combined extracts were washed with 1 N HCl and brine, then dried over magnesium sulfate, filtered and solvent removed under vacuum to afford 17.3 g (68.7 mmol, 99%) of the product. 1H NMR (200 MHz, CDCl3): δ 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°
  5. additionslowly acidified to pH 2 (paper) by dropwise addition of 6 N HCl
  6. extractionThis mixture was extracted with ether (6×)
  7. washcombined extracts were washed with 1 N HCl and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-eddbca2bd2f34242b5dec812b89b9648
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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