Hydrochloric Acid → [(3S)-1-{5-[methyl(tetrahydro-2H-pyran-4-yl)carbamoyl]-6-(propylthio)pyridin-2-yl}piperidin-3-yl]acetic acid

HRID 1187380노트

반응식

HRID 1187380 반응식
[OH-].[Na+].[CH3:3][N:4]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][C:24]([O:26]C)=[O:25])[CH2:18]2)=[N:11][C:12]=1[S:13][CH2:14][CH2:15][CH3:16])=[O:6].Cl>O.CO.CCOC(C)=O.C(Cl)Cl>[CH3:3][N:4]([CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[C:5]([C:7]1[CH:8]=[CH:9][C:10]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][C:24]([OH:26])=[O:25])[CH2:18]2)=[N:11][C:12]=1[S:13][CH2:14][CH2:15][CH3:16])=[O:6]

참가 물질

8

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59830659methyl [(3S)-1-{5-[methyl(tetrahydro-2H-pyran-4-yl)carbamoyl]-6-(propylthio)pyridin-2-yl}piperidin-3-yl]acetate

생성물 1

HCID 59830715[(3S)-1-{5-[methyl(tetrahydro-2H-pyran-4-yl)carbamoyl]-6-(propylthio)pyridin-2-yl}piperidin-3-yl]acetic acid수율 100%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
18 °C

실험 절차

A solution of sodium hydroxide (0.130 g, 3.25 mmol) in water (1.63 mL) was added dropwise to a stirred solution of methyl [(3S)-1-{5-[methyl(tetrahydro-2H-pyran-4-yl)carbamoyl]-6-(propylthio)pyridin-2-yl}piperidin-3-yl]acetate (293 mg, 0.65 mmol) in MeOH (5 mL) at 18° C., over a period of 1 minute. The resulting solution was stirred at 18° C. for 20 hours. The reaction mixture was adjusted to pH 4.5 with 2M HCl and the reaction mixture was diluted with EtOAc (50 mL), and washed sequentially with water (20 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The residue was dissolved in DCM (10 ml) and the slight suspension filtered through a nylon millipore filter to remove the solid. Evaporation gave the product, [(3S)-1-{5-[methyl(tetrahydro-2H-pyran-4-yl)carbamoyl]-6-(propylthio)pyridin-2-yl}piperidin-3-yl]acetic acid (281 mg, 100%), as a white solid

후처리

  1. washwashed sequentially with water (20 mL) and saturated brine (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. filtrationthe slight suspension filtered through a nylon
  7. filtrationmillipore filter
  8. customto remove the solid
  9. customEvaporation

출처 및 근거

ORD 기록
ord-f15b3de780904459afe9f78808cdcbf4
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673938B2

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