L-Serine → methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate

HRID 37263

反応式

HRID 37263 の反応式
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[C:8](=O)([O-])O.[Na+].[N+:13]([C:16]1[CH:26]=[CH:25][C:19]([CH2:20][O:21][C:22](Cl)=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>O.C(OCC)C>[OH:4][CH2:3][C@H:2]([NH:1][C:22]([O:21][CH2:20][C:19]1[CH:25]=[CH:26][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1)=[O:23])[C:5]([O:7][CH3:8])=[O:6]

参加物

6

反応物 3

HCID 5951L-SerineHCID 782054-Nitrobenzyl chloroformate2 回HCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 57056522methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate収率 24.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a stirred solution of L-serine (3.5 g) and sodium hydrogen carbonate (7.5 g) in water (46 ml) was added 4-nitrobenzyloxycarbonyl chloride (6.4 g) in diethyl ether (10 ml) at ambient temperature. After stirring for 2 hours, to the solution were added 4-nitrobenzyloxycarbonyl chloride (6.4 g) in diethyl ether (10 ml), and sodium hydrogen carbonate (3.6 g). After stirring for 3 hours, the aqueous layer was separated and washed with ethyl acetate. After adjusting the pH to 2 with concentrated hydrochloric acid, the aqueous solution was extracted twice with ethyl acetate, dried over magnesium sulfate and evaporated. To the residue were added methanol (40 ml) and concentrated sulfuric acid (0.7 ml), and the solution was stirred at 50°-55° C. for 2.5 hours. To the mixture was added triethylamine (4.2 ml) and the mixture was evaporated in vacuo. The resulting residue was poured into a mixture of ethyl acetate and water. The organic layer was separated, washed twice with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (300 ml) and eluted with a mixture of acetone and dichloromethane (8:92, V/V) to give methyl (2S)-3-hydroxy-2-[(4-nitrobenzyloxycarbonyl)amino]propionate (2.14 g).

後処理

  1. stirringAfter stirring for 3 hours
  2. customthe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. extractionthe aqueous solution was extracted twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. additionTo the residue were added methanol (40 ml) and concentrated sulfuric acid (0.7 ml)
  8. stirringthe solution was stirred at 50°-55° C. for 2.5 hours
  9. additionTo the mixture was added triethylamine (4.2 ml)
  10. customthe mixture was evaporated in vacuo
  11. additionThe resulting residue was poured into a mixture of ethyl acetate and water
  12. customThe organic layer was separated
  13. washwashed twice with brine
  14. dry with materialdried over magnesium sulfate
  15. customevaporated
  16. customThe residue was chromatographed on silica gel (300 ml)
  17. washeluted with a mixture of acetone and dichloromethane (8:92, V/V)

出典と根拠

ORDレコード
ord-6c61435520ec4c3591e0370b97cba174
出典データセット
uspto-grants-1995_05
特許番号
US05420122

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