Tetrahydrofuran → 5-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid

HRID 1616633노트

반응식

HRID 1616633 반응식
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:20])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:12]=1.C1COCC1.[OH-].[Na+]>CCO>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])[O:9][C:10]=1[CH3:20]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 684911055-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

생성물 1

HCID 684930945-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Combine 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (2.9 g, 10.0 mmol) with THF (3 mL), EtOH (3 mL) and 2N NaOH (20 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 2.0-3.0 with aq HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid (2.14 g, 78%). MS (ES): (M+1)+ 276.2 m/z.

후처리

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the extracts over Na2SO4
  5. concentrationbefore concentrating

출처 및 근거

ORD 기록
ord-0e6da45e38bb43b9ab755b4298f03c4a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765796B2

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