Sodium Hydroxide → [2-(7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid

HRID 1188993노트

반응식

HRID 1188993 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:25]=[N:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:25]=[N:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][N:16]=1)=[CH:8]2

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 70963862Ethyl [2-(7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate

생성물 1

HCID 67118501[2-(7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid수율 93%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl [2-(7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (11.06 g) was dissolved in a mixture of tetrahydrofuran (100 mL) and ethanol (100 mL). To the mixture was added 1M aqueous sodium hydroxide solution (37 mL) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and 1M hydrochloric acid (37 mL) was added to the mixture. The resulting yellow suspension was filtered to collect a yellow solid. The solid was dissolved in ethyl acetate-tetrahydrofuran. The solution was dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (9.65 g, 93%) as a yellow solid. MS 462 (MH+).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. addition1M hydrochloric acid (37 mL) was added to the mixture
  4. filtrationThe resulting yellow suspension was filtered
  5. customto collect a yellow solid
  6. dissolutionThe solid was dissolved in ethyl acetate-tetrahydrofuran
  7. dry with materialThe solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe residual solid was washed with diethyl ether

출처 및 근거

ORD 기록
ord-c52ec2425e764205b9416313106d561f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673942B2

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