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

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

Reactant 3

HCID 887Methanol

HCID 11430Potassium Carbonate

HCID 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.