Lithium Hydroxide → 3-Cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid

HRID 1936239노트

반응식

HRID 1936239 반응식
C[O:2][C:3](=[O:24])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]([OH:23])([CH3:22])[CH2:20][CH3:21])=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[C:18][C:19]([OH:23])([CH3:22])[CH2:20][CH3:21])=[CH:13][CH:12]=2)[C:3]([OH:24])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 674841063-Cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid methyl ester

생성물 1

HCID 224653023-Cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid수율 91.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid methyl ester (656 mg, 1.99 mmol) in methanol (10 mL) and water (10 mL) was treated with lithium hydroxide (920 mg, 21.9 mmol). The reaction mixture was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (40 mL). This solution was acidified to pH=2 with concentrated hydrochloric acid and then extracted with ethyl acetate (2×40 mL). The combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(3-hydroxy-3-methyl-pent-1-ynyl)-phenyl]-propionic acid (570 mg, 91%) as a tan solid: mp 91-94° C.; EI-HRMS m/e calcd for C20H26O3 (M+) 314.1881, found 314.1872.

후처리

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (40 mL)
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic extracts were then washed with a half-saturated sodium chloride solution (1×40 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a6ff0b5489ba497bb7c4eb7096b9a497
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06388071B2

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