D-Glutamic Acid → (R)-5-oxo-2-tetrahydrofurancarboxylic acid

HRID 500345

반응식

HRID 500345 반응식
N[C@@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].N([O-])=O.[Na+]>O.Cl>[O:9]=[C:8]1[O:10][C@@H:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 23327D-Glutamic AcidHCID 23668193Sodium Nitrite

생성물 1

HCID 104532(R)-5-oxo-2-tetrahydrofurancarboxylic acid수율 57.1%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매2회

실험 절차

To a mixture of D-glutamic acid (1, 25 g, 170 mmol) in water (67 mL) and conc. HCl (35 mL) at 0° C. with stirring was added a solution of NaNO2 (17.5 g, 253.6 mmol) in water (37.5 mL) over a period of 4 h, and then the resulting clear solution was stirred at room temperature overnight. After removal of the solvent by evaporation in vacuo, the residue was treated with EtOAC (80 mL) and filtered. The filtrate was dried over Na2SO4, and concentrated. The residue, after crystallization from EtOAc/benzene/hexane, afforded the title compound 2 as a white crystalline solid (12.63 g, 57%). M.P. 71-73° C.; 1H NMR (400 MHz, CD3OD) δ 4.20 (m, 1H, CHO), 1.8-2.3 (m, 4H, CH2CH2).

후처리

  1. stirringthe resulting clear solution was stirred at room temperature overnight
  2. customAfter removal of the solvent
  3. customby evaporation in vacuo
  4. additionthe residue was treated with EtOAC (80 mL)
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue, after crystallization from EtOAc/benzene/hexane

출처 및 근거

ORD 기록
ord-bc4cc98b77dc4eb39a46e3f8a01cd65c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772208B2

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