Sodium Hydroxide → (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclopentyl-acrylic acid

HRID 1936399노트

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HRID 1936399 반응식
C[O:2][C:3](=[O:24])/[C:4](/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]([CH3:22])=[N:20][N:19]=[N:18]2)=[C:13]([Cl:23])[CH:12]=1)=[CH:5]/[CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[Cl:23][C:13]1[CH:12]=[C:11](/[C:4](=[CH:5]\[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)/[C:3]([OH:24])=[O:2])[CH:16]=[CH:15][C:14]=1[N:17]1[C:21]([CH3:22])=[N:20][N:19]=[N:18]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 69691324(E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclopentyl-acrylic acid methyl ester

생성물 1

HCID 12019651(E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclopentyl-acrylic acid수율 101.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
47.5 °C

실험 절차

A solution of (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclopentyl-acrylic acid methyl ester (160 mg, 0.46 mmol) in ethanol (5 mL) was treated with a 1N aqueous sodium hydroxide solution (1 mL). The solution was heated at 45-50° C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was concentrated in vacuo to remove ethanol. The residue was diluted with water (10 mL) and extracted with diethyl ether (1×30 mL) to remove any neutral impurities. The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and the resulting acid was extracted into ethyl acetate (2×20 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclopentyl-acrylic acid (155 mg, 100%) as a white solid: mp 216-219° C.; EI-HRMS m/e calcd for C16H17ClN4O2 (M+) 332.1040, found 332.1048.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove ethanol
  3. additionThe residue was diluted with water (10 mL)
  4. extractionextracted with diethyl ether (1×30 mL)
  5. customto remove any neutral impurities
  6. extractionthe resulting acid was extracted into ethyl acetate (2×20 mL)
  7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-54aeec1a04d8469a9832226f6bc39d6e
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06388088B1

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