Sodium Hydroxide → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid

HRID 229861

반응식

HRID 229861 반응식
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])[N:7]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:6]=1[CH3:27])=[O:4].[OH-].[Na+]>O1CCOCC1.O.C(OCC)C>[CH3:27][C:6]1[N:7]([CH2:21][C@@H:22]2[CH2:26][CH2:25][CH2:24][O:23]2)[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:18])([F:20])[F:19])=[CH:9][C:5]=1[C:3]([OH:4])=[O:2]

참가 물질

6

반응물 2

HCID 14798Sodium HydroxideHCID 690232432-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester

생성물 1

HCID 690199812-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid수율 93.5%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 171 mg of 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester in dioxane (4 ml) and water (4 ml) was added 1.3 ml of a 1N solution of sodium hydroxide. The reaction mixture was heated at reflux for 20 hours. After such time the reaction mixture was allowed to cool down to room temperature. The mixture was diluted with diethyl ether and extracted with 1N sodium hydroxide solution. Water phases were pooled, acidified with 2N solution of hydrochloride acid and extracted twice with diethyl ether. The organic phases were pooled, washed with brine and dried with MgSO4. Solvent was removed to give 154 mg of the title compound as brownish oil; MS (ISP) 368.0 (M−H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. extractionextracted with 1N sodium hydroxide solution
  4. extractionextracted twice with diethyl ether
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. customSolvent was removed

출처 및 근거

ORD 기록
ord-5421a429daa2457c8c3e34ed94cd0749
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563910B2

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