Methanol → HCID 59314305, compound

HRID 1047917Notes

Reaction equation

HRID 1047917 reaction equation
C([O:3][C:4]([C:6]1([C:15](=[O:27])[NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:18]=2[CH2:19][CH2:20][NH:21][CH2:22]3)[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>[CH2:22]1[C:23]2[C:18](=[C:17]([NH:16][C: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:27])[CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:20][NH:21]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 312751,4-DioxaneHCID 59314223HCID 59314223, compound

Product 1

HCID 59314305HCID 59314305, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A 250 mL round bottom flask containing 2-(1,2,3,4-tetrahydro-isoquinolin-5-ylcarbamoyl)-indan-2-carboxylic acid ethyl ester (322, 440 mg, 1.21 mmoles) is charged with 1,4-dioxane (7 mL) and MeOH (7 mL). A stirring bar is added and stirring is initiated. After dissolution, water (3.5 mL) is added followed by the LiOH monohydrate (128 mg, 3.05 mmol). After 18 h, tlc analysis (silica, 10% MeOH/DCM) indicates that the starting material is completely consumed. Amberlyst highly acidic exchange resin (1 g) is added to the reaction flask. The reaction is capped and allowed to stir at ambient temperature. After 24 h, the contents of the flask are filtered through a pad of Celite. The solvent is removed from the filtrate. The resultant residue is reconstituted with iPrOH/toluene (1:1, 25 mL). The solvent is removed in vacuo. This process is repeated twice. Pumping to constant weight provides an off-white solid (400 mg, 99%).

Workup

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionAmberlyst highly acidic exchange resin (1 g) is added to the reaction flask
  5. customThe reaction is capped
  6. stirringto stir at ambient temperature
  7. waitAfter 24 h
  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 in vacuo

Sources & evidence

ORD record
ord-be023fa813aa4e799c64169edec918eb
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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