Water → 8-(2-Carboxy-indan-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1047839Notes

Reaction equation

HRID 1047839 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18](=[O:34])[NH:19][C:20]3([C:29]([O:31]CC)=[O:30])[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].O>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([C:18](=[O:34])[NH:19][C:20]3([C:29]([OH:31])=[O:30])[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21]3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593142148-(2-Ethoxycarbonyl-indan-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 593141048-(2-Carboxy-indan-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product (217) (2.46 g, 5.3 mmol) and KOH (2.5 g, 45 mmol) is dissolved in EtOH (20 mL) and water (1 mL) under a water bath. The water bath is removed when the KOH is completely dissolved and the resulting reaction solution is stirred at RT for 3 h. After concentration in vacuo, the residue is dissolved in water (50 mL) and acidified with conc. HCl until no more white precipitate came out of the water. The precipitate is filtered to give a pure product (218) as white solid (1.4 g, 61%).

Workup

  1. customThe water bath is removed when the KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (50 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-2365f42f1bfb4723a4b07ad0cee7f9e9
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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