Sodium Hydroxide → HCID 21955230, compound

HRID 2213051Notes

Reaction equation

HRID 2213051 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:19])[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:8]([CH3:11])([CH3:10])[CH3:9]>CO>[CH3:17][C:15]([CH3:18])([O:14][C:12]([N:7]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:6][C:5]([OH:19])=[O:4])=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21955129HCID 21955129, compound

Product 1

HCID 21955230HCID 21955230, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (4M, 5 mL) was added to a solution of N-[(1,1-dimethylethoxy)carbonyl]-N-(1,1-dimethylethyl)glycine methyl ester (Description 158, 2.0 g, 8.2 mmol) in methanol (10 mL) and the mixture was stirred at room temperature for 40 hours. The solvent was evaporated under reduced pressure, hydrochloric acid (2M, 20 mL) was added and the mixture was extracted with dichloromethane (3×40 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (1.6 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.41 (9H, s), 1.46 (9H, s), and 4.08 (2H, s).

Workup

  1. customThe solvent was evaporated under reduced pressure, hydrochloric acid (2M, 20 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (3×40 mL)
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68cdcf84d8de4dc9a2b01f06444e00c1
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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