Methanol → HCID 25161181, compound

HRID 1047913Notes

Reaction equation

HRID 1047913 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:30])[C:17]2[CH:22]=[C:21]([Br:23])[CH:20]=[C:19]([CH3:24])[C:18]=2[O:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.O>CO.C(Cl)Cl>[Br:23][C:21]1[CH:20]=[C:19]([CH3:24])[C:18]([O:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)=[C:17]([CH:22]=1)[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:30]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 312751,4-DioxaneHCID 59314093HCID 59314093, compound

Product 1

HCID 25161181HCID 25161181, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A 30 mL reaction vial is charged with 2-(5-bromo-2-cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (0.29 g, 0.61 mmoles) is charged with 1,4-dioxane (4 mL) and MeOH (4 mL). A stirring bar is added and stirring is initiated. After dissolution, water (2 mL) is added followed by the LiOH monohydrate (65 mg, 1.55 mmol). After 38 h, tlc analysis (silica, 10% MeOH/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%, ˜6 mL). The contents of the flask are poured into a separatory funnel which contains EtOAc (30 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic phases are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated by pumping to constant weight to give off white solid (0.26 g, 95%).

Workup

  1. customA 30 mL reaction
  2. additionA stirring bar is added
  3. additionis added
  4. customis completely consumed
  5. additionby slowly adding dilute aqueous HCl (3%, ˜6 mL)
  6. additionThe contents of the flask are poured into a separatory funnel which
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (20 mL)
  9. washThe combined organic phases 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-b388d53660be4af6897fb35517fbadfc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

Loading…