Oxalic acid dihydrate → [Rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester

HRID 1065018노트

반응식

HRID 1065018 반응식
O.O.C(O)(=O)C(O)=O.[CH2:9]([O:11][C:12](=[O:37])[CH:13]([O:34][CH2:35][CH3:36])[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22]CC2C=CC=CC=2)=[CH:18][C:17]=1[O:30][CH:31]([CH3:33])[CH3:32])O)[CH3:10]>C(O)(C)C.[Pd]>[CH2:9]([O:11][C:12](=[O:37])[CH:13]([O:34][CH2:35][CH3:36])[CH2:14][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[O:30][CH:31]([CH3:32])[CH3:33])[CH3:10]

참가 물질

5

반응물 2

HCID 61373Oxalic acid dihydrateHCID 69280524[Rac]-3-(4-benzyloxy-2-isopropoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid ethyl ester

생성물 1

HCID 69280498[Rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 3776Isopropanol용매

실험 절차

0.80 g of Pd/C (10%) and 6.0 g of oxalic acid dihydrate were added under argon to 3.20 g (7.95 mmol) of [rac]-3-(4-benzyloxy-2-isopropoxy-phenyl)-2-ethoxy-3-hydroxy-propionic acid ethyl ester [mixture of diastereomers] dissolved in 60 ml of isopropanol. This solution was stirred for 24 hours at room temperature and 50 bar H2. Filtration over dicalite and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9:1 to 1:1) left 0.69 g (29% of theory) of [rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester as yellow oil.

후처리

  1. filtrationFiltration
  2. customover dicalite and evaporation of the solvents
  3. waitleft 0.69 g (29% of theory) of [rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester as yellow oil

출처 및 근거

ORD 기록
ord-06db83acd7a84b10accff7ce374ed98e
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969725B2

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