Potassium Hydroxide → 2-((tert-Butoxycarbonyl)amino)-3-ethoxy-3-oxopropanoic acid

HRID 1923992Notes

Reaction equation

HRID 1923992 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]([O:17]CC)=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O.O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonate

Product 1

HCID 110110222-((tert-Butoxycarbonyl)amino)-3-ethoxy-3-oxopropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a solution of 1,3-diethyl 2-{[(tert-butoxy)carbonyl]amino}propanedioate XCVI (2.22 g, 8 mmol) in a mixture of ethanol/water (45 mL/5 mL) was added KOH (0.45 g, 8 mmol) in water (3 mL) dropwise. The reaction mixture was stirred for 1.5 hours. The ethanol was evaporated and the residue was acidified to pH=2 by 2 M HCl and washed by DCM. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated to give 2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid XCVII as crystals (1.68 g, 6.8 mmol, 85% yield). 1H NMR (CDCl3) 1.31 (t, J=7 Hz, 3H), 1.41-1.45 (m, 9H), 4.23-4.31 9 m, 2H), 4.76 (d, J=4 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 10.84 (brs, 1H); ESIMS found for C10H17NO6 m/z 248 (M+H).

Workup

  1. customThe ethanol was evaporated
  2. washwashed by DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-513c80883a7b4ca497e2be56435f9217
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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