Methanol → HCID 59314352、化合物

HRID 1047812ノート

反応式

HRID 1047812 の反応式
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[S:22][C:21]3[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=3[C:19]=2[CH3:28])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.CO.O.[Li+].[OH-]>CC(O)C.C(Cl)Cl>[Cl:27][C:25]1[CH:24]=[CH:23][C:21]2[S:22][C:18]([C:16]([NH:15][C:6]3([C:4]([OH:5])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[O:17])=[C:19]([CH3:28])[C:20]=2[CH:26]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59314205HCID 59314205、化合物

生成物 1

HCID 59314352HCID 59314352、化合物収率 72.9%

試薬・触媒・溶媒 1

HCID 21966342Isopropanol methylene chloride溶媒

実験手順

40 mL vial containing the 2-[(5-chloro-3-methyl-benzo[b]thiophene-2-carbonyl)-amino]-indane-2-carboxylic acid ethyl ester (0.53 g, 1.28 mmol) is charged with MeOH (7.5 mL) and a stirring bar is added. Stirring is initiated. After dissolution, water (3.8 mL) is added followed by the LiOH (134 mg, 3.20 mmol). After 36 h, tlc analysis (silica, 5% i-PrOH/DCM) indicates that the starting material is completely consumed. The pH of the reaction mixture is carefully adjusted to pH 2 by slowly adding dilute aqueous HCl (3%, ˜10 mL). The contents of the flask are poured into a reparatory funnel containing EtOAc (30 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated to yield 360 mg of amorphous white solid.

後処理

  1. additionis added
  2. additionis added
  3. customis completely consumed
  4. additionby slowly adding dilute aqueous HCl (3%, ˜10 mL)
  5. additionThe contents of the flask are poured into a reparatory funnel
  6. additioncontaining EtOAc (30 mL)
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (20 mL)
  9. washThe combined organic extracts are washed with water (20 mL) and brine (20 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-612f94c7821b487688586d939606c88f
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

読み込み中…