Lithium Hydroxide → HCID 60142091, compound

HRID 572495Notes

Reaction equation

HRID 572495 reaction equation
C[O:2][C:3](=[O:37])[CH:4]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:5]1[N:6]([CH3:31])[C:7](=[O:30])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([O:26][CH2:27][CH2:28][OH:29])[CH:9]=2.[Li+].[OH-]>C1COCC1>[C:33]([O:32][CH:4]([C:5]1[N:6]([CH3:31])[C:7](=[O:30])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([O:26][CH2:27][CH2:28][OH:29])[CH:9]=2)[C:3]([OH:37])=[O:2])([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68295230HCID 68295230, compound

Product 1

HCID 60142091HCID 60142091, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-Butoxy-[7-(2-hydroxy-ethoxy)-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester (30 mg, 0.059 mmol) in THF (3 ml), was added 1N LiOH (3 mL). The resultant mixture was stirred at 70° C. overnight. The solvent was removed in vacuo; the reaction mixture was acidified by 1N HCl solution to pH 5-6. The white solid was filtered to afford the title product (9 mg, 30.8%). LCMS (10-80 AB—2MIN.M): Rt=1.190, purity=97.3%, M+1=496.

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationThe white solid was filtered

Sources & evidence

ORD record
ord-580853f32dae492e8e784b2aa6a3a7d3
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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