Sodium Hydroxide → 3-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid

HRID 2306388노트

반응식

HRID 2306388 반응식
C[O:2][C:3](=[O:27])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N:21]2[C:25]([CH3:26])=[N:24][N:23]=[N:22]2)[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[C:13]([N:21]3[C:25]([CH3:26])=[N:24][N:23]=[N:22]3)[CH:12]=2)[C:3]([OH:27])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 696913393-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]propionic acid methyl ester

생성물 1

HCID 184343533-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid수율 89.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid methyl ester (102 mg, 0.26 mmol) in ethanol (3 mL) was treated with a 1N aqueous sodium hydroxide solution (0.6 mL). The solution was 3heated at 45-50° C. for 5 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 (20 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 (2×25 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 3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid (88 mg, 89%) as an amorphous white solid: EI-HRMS m/e calcd for C17H22N4O4S (M+) 378.1362, found 378.1364.

후처리

  1. customat 45-50° C.
  2. customfor 5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove ethanol
  5. additionThe residue was diluted with water (20 mL)
  6. extractionextracted with diethyl ether (1×30 mL)
  7. customto remove any neutral impurities
  8. extractionthe resulting acid was extracted into ethyl acetate (2×25 mL)
  9. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-96de154120414509b59fc1f809d67efd
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441180B1

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