Acetic Acid → 2-{[(Tert-butoxy)carbonyl]amino}-3-(1,3-oxazol-5-yl)propanoic acid

HRID 635642Notes

Reaction equation

HRID 635642 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH2:20][C:21]1[O:25][CH:24]=[N:23][CH:22]=1)(C(OCC)=O)[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>O.C(O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:10]([OH:12])=[O:11])[CH2:20][C:21]1[O:25][CH:24]=[N:23][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 70092767Diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate

Product 1

HCID 212590172-{[(Tert-butoxy)carbonyl]amino}-3-(1,3-oxazol-5-yl)propanoic acidYield 113.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.5 g of diethyl 2-(tert-butoxyformamido)-2-[(5-oxazolyl)methyl]malonate were dissolved in 1.5 ml of water and 1.5 ml of ethanol. 337 mg of sodium hydroxide were added and the mixture was stirred overnight at room temperature. The mixture was then acidified to pH 5 with acetic acid and the solvent was removed by evaporation. The residue was dissolved in 5 ml of toluene and 0.64 ml of triethylamine was added. The mixture was heated at reflux for 2 hours and then the solvents were evaporated. Ethyl acetate was added and the solution was washed with saturated aqueous citric acid solution. The organic layer was dried over magnesium sulphate to give 1.224 g of crude N-(tert-butoxycarbonyl)-3(5-oxazolyl)-DL-alanine, 1H NMR (250 MHZ, d6-DMSO) δ: 1.4 (s,9H), 3.0-3.3 (m,2H), 6.95 (s,1H), 7.25 (m, 1H), 8.3 (s,1H).

Workup

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in 5 ml of toluene
  3. addition0.64 ml of triethylamine was added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 2 hours
  6. customthe solvents were evaporated
  7. additionEthyl acetate was added
  8. washthe solution was washed with saturated aqueous citric acid solution
  9. dry with materialThe organic layer was dried over magnesium sulphate

Sources & evidence

ORD record
ord-1bfcbbf8b8184b37853a49a3f7dd00ea
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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