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

HRID 635642ノート

反応式

HRID 635642 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1bfcbbf8b8184b37853a49a3f7dd00ea
出典データセット
uspto-grants-2001_02
特許番号
US06187905B1

反応ノート

読み込み中…