Methanol → HCID 59314282, compound

HRID 1047943Notes

Reaction equation

HRID 1047943 reaction equation
C([O:3][C:4]([C:6]1([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH:25]([CH3:27])[CH3:26])[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>[CH:25]([O:24][C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][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)([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 59314341HCID 59314341, compound

Product 1

HCID 59314282HCID 59314282, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask containing 2-(2-isopropoxy-3-methyl-benzylamino)-indan-2-carboxylic acid ethyl ester (365, 360 mg, 0.98 mmol) is charged with 1,4-dioxane (3 mL) and MeOH (3 mL). A stirring bar is added and stirring is initiated. After dissolution, water (1.5 mL) is added followed by the LiOH monohydrate (104 mg, 2.47 mmol). After 39 h, tlc analysis (silica, 50% EtOAc/Heptanes) indicates that the starting material is completely consumed. Amberlyst highly acidic exchange resin (0.5 g) is added to the reaction vial. The reaction is capped and allowed to stir at ambient temperature. After 15 days, the contents of the flask are filtered through a pad of Celite. The solvent is removed from the filtrate. The residue is reconstituted with iPrOH/toluene (20+20 mL) and the solvent is removed. This process is repeated 1 time. Pumping to constant weight provided white solid (0.24 g, 72%).

Workup

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionAmberlyst highly acidic exchange resin (0.5 g) is added to the reaction vial
  5. customThe reaction is capped
  6. stirringto stir at ambient temperature
  7. waitAfter 15 days
  8. filtrationthe contents of the flask are filtered through a pad of Celite
  9. customThe solvent is removed from the filtrate
  10. customthe solvent is removed

Sources & evidence

ORD record
ord-77660a37cb9246b28184804c999b25e6
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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