Citric Acid → (2R)-3-benzyloxy-2-(tert-butoxycarbonylmethylamino)propionic acid

HRID 495783

反応式

HRID 495783 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][C:15](OC(C)(C)C)=O)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[H-].[Na+].C(O)(=O)[CH2:27][C:28]([CH2:33]C(O)=O)([C:30](O)=O)[OH:29].[O:39]1CCC[CH2:40]1>>[CH2:1]([O:8][CH2:9][C@@H:10]([NH:14][CH2:15][C:40]([O:29][C:28]([CH3:27])([CH3:30])[CH3:33])=[O:39])[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 5

HCID 311Citric AcidHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

生成物 1

HCID 54443421(2R)-3-benzyloxy-2-(tert-butoxycarbonylmethylamino)propionic acid

反応条件

温度
0 °C

実験手順

(2R)-3-Benzyloxy-2-tert-butoxycarbonylaminopropionic acid (7.0 g; 23.7 mmol) was dissolved in dry tetrahydrofuran and iodomethane (11.9 mL; 189 mmol) was added. The reaction mixture was cooled to OIC and sodium hydride (60% in mineral oil) (2.73 g; 71 mmol) was added. The reaction mixture was left 3 days without stirring at 0° C. Citric acid (5%) was added until pH 2.5. Tetrahydrofuran was removed in vacuo and the residue was extracted with methylene chloride (3×100 mL). The organic phase was dried (magnesium sulfate) and evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL) and dicyclohexylamine (10 mL) and is heptane (100 mL) were added. The reaction mixture was left 3 days without stirring at 0° C. The reaction mixture was filtered to afford 5.78 g of (2R)-3-benzyloxy-2-(tert-butoxycarbonylmethylamino)propionic acid.

後処理

  1. additionwas added
  2. customTetrahydrofuran was removed in vacuo
  3. extractionthe residue was extracted with methylene chloride (3×100 mL)
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in diethyl ether (20 mL)
  7. additionwere added
  8. waitThe reaction mixture was left 3 days
  9. stirringwithout stirring at 0° C
  10. filtrationThe reaction mixture was filtered

出典と根拠

ORDレコード
ord-f5b5b9ca84d0473083802f5be213249f
出典データセット
uspto-grants-2005_09
特許番号
US06939880B2

関連ノート

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