Sodium Hydroxide → HCID 67193625, compound

HRID 2366969Notes

Reaction equation

HRID 2366969 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67195169methyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

Product 1

HCID 67193625HCID 67193625, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoate (for a preparation see Intermediate 107) (20 mg, 0.047 mmol) in ethanol (0.5 mL) was added NaOH (1M in water, 0.188 mL, 0.188 mmol) and the resulting mixture was stirred at room temperature for 3 h then concentrated in vacuo. Purification of the residue using MDAP gave 4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoic acid (12 mg, 0.029 mmol, 62%) as a white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification of the residue

Sources & evidence

ORD record
ord-482c1b5b00d3415d8dec3f1ef8adf54b
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…