Methanol → HCID 59314352, compound

HRID 1047812Notes

Reaction equation

HRID 1047812 reaction equation
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

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59314205HCID 59314205, compound

Product 1

HCID 59314352HCID 59314352, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 21966342Isopropanol methylene chlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-612f94c7821b487688586d939606c88f
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…