Lithium Hydroxide → [7-(4-t-Butoxycarbonylpiperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetic acid

HRID 1377525Notes

Reaction equation

HRID 1377525 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:11][CH:12]=2)[C:7]1=[O:29])C.[Li+].[OH-]>CO>[C:25]([O:24][C:22]([N:19]1[CH2:18][CH2:17][N:16]([C:10]2[CH:9]=[C:8]3[C:13]([CH2:14][CH2:15][N:6]([CH2:5][C:4]([OH:30])=[O:3])[C:7]3=[O:29])=[CH:12][CH:11]=2)[CH2:21][CH2:20]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10598069Ethyl [7-(4-t-butoxycarbonylpiperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetate

Product 1

HCID 11794693[7-(4-t-Butoxycarbonylpiperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl [7-(4-t-butoxycarbonylpiperazin-1-yl)-3,4-dihydro-1(1H)-isoquinolinone-2-yl]acetate (1-4) (2.9 g, 6.95 mmol), 1N LiOH (20.9 mL, 20.9 mmol) and MeOH (50 mL) were stirred for 16 hours at room temperature. The solvent was removed, the residue was taken up in EtOAc and washed with 1N HCl. Repeated extraction of the aqueous phase followed by washing of the bulked organic layers with brine (5 mL), drying (MgSO4) and evaporation afforded 1-5 as a solid. 1H NMR (CD3OD): d1.48 (9H, s), 2.99 (2H, t), 3.20 (4H, m), 3.62 (6H, m), 4.31 (2H, s), 7.22 (2H, s), 7.60 (1H, s).

Workup

  1. customThe solvent was removed
  2. washwashed with 1N HCl
  3. extractionextraction of the aqueous phase
  4. washby washing of the bulked organic layers with brine (5 mL)
  5. customdrying
  6. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-f5090744201b4100aeca56b6cb08a835
Source dataset
uspto-grants-1997_09
Patent number
US05665723

Reaction notes

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