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Sodium Hydroxide → 2-[3-Chloro-4-(5-trifluoromethyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid

HRID 841217
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HRID 841217 반응식
C[O:2][C:3](=[O:28])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([C:23]([F:26])([F:25])[F:24])=[N:21][N:20]=[N:19]2)=[C:14]([Cl:27])[CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[Cl:27][C:14]1[CH:13]=[C:12]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:28])=[O:2])[CH:17]=[CH:16][C:15]=1[N:18]1[C:22]([C:23]([F:26])([F:24])[F:25])=[N:21][N:20]=[N:19]1
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4

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HCID 14798Sodium HydroxideHCID 696912642-[3-Chloro-4-(5-trifluoromethyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid methyl ester

생성물 1

HCID 120196472-[3-Chloro-4-(5-trifluoromethyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid수율 61.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
47.5 °C

실험 절차

A solution of 2-[3-chloro-4-(5-trifluoromethyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid methyl ester (634 mg, 1.52 rumol) in ethanol (10 mL) was treated with a 1N aqueous sodium hydroxide solution (3 mL). The solution was heated at 45-50° C. for 5 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (50 mL) and extracted with diethyl ether (1×60 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 2-[3-chloro-4-(5-trifluoromethyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid (375 mg, 61%) as a viscous oil: EI-HRMS m/e calcd for C17H18ClF3N4O2 (M+) 402.1070, found 402.1067.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove ethanol
  3. additionthe residue was diluted with water (50 mL)
  4. extractionextracted with diethyl ether (1×60 mL)
  5. customto remove any neutral impurities
  6. extractionThe resulting acid was extracted into ethyl acetate (2×50 mL)
  7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2e9e29d7e5b94718b1219a2b2ef479d5
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06369232B1

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