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

HRID 2306388ノート

反応式

HRID 2306388 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-96de154120414509b59fc1f809d67efd
出典データセット
uspto-grants-2002_08
特許番号
US06441180B1

反応ノート

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