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

HRID 1187380ノート

反応式

HRID 1187380 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
18 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-f15b3de780904459afe9f78808cdcbf4
出典データセット
uspto-grants-2014_03
特許番号
US08673938B2

反応ノート

読み込み中…