Methanol → (R)-2-(1-Hydroxycycloheptyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

HRID 418525Notes

Reaction equation

HRID 418525 reaction equation
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:30])[C:14]=2[NH:18][C:19](=[O:29])[CH2:20][C:21]2([OH:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]1=[O:31])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>>[OH:28][C:21]1([CH2:20][C:19]([NH:18][C:14]2[C:13]([CH3:30])=[CH:12][CH:11]=[C:10]3[C:15]=2[CH:16]=[CH:17][N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[C:9]3=[O:31])=[O:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59845716(R)-2-(5-(2-(1-Hydroxycycloheptyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Product 1

HCID 25012146(R)-2-(1-Hydroxycycloheptyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Procedure

A round bottom flask was charged with (R)-2-(5-(2-(1-hydroxycycloheptyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (100.00 mg, 0.14 mmol), potassium carbonate (58.0 mg, 0.000420 mol) and methanol (4 mL, 0.1 mol) and the reaction mixture stirred at room temperature 1 hour. The solvent was removed under reduced pressure and the residue was purified by reverse phase preparative HPLC to afford the product.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by reverse phase preparative HPLC
  3. customto afford the product

Sources & evidence

ORD record
ord-d566f67c395b4022b1f8c47de3eeab0e
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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