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

HRID 635642노트

반응식

HRID 635642 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1bfcbbf8b8184b37853a49a3f7dd00ea
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187905B1

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