Sodium Hydroxide → HCID 86669464, compound

HRID 2041782Notes

Reaction equation

HRID 2041782 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([O:19]C)=[O:18])=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=3)[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[CH:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67207123HCID 67207123, compound

Product 1

HCID 86669464HCID 86669464, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoate (for a preparation see Example 175) (14.5 mg, 0.035 mmol) in methanol (1 mL) was added NaOH (2M in water, 0.5 mL, 1.000 mmol) and the resulting mixture was stirred at room temperature for 100 min then was concentrated under a stream of nitrogen. The residue was dissolved in water (0.2 mL) and methanol (0.8 mL) before being purified by MDAP (modifier: formic acid) to give 3-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]benzoic acid:formic acid 1:3 (14.3 mg, 85% yield).

Workup

  1. concentrationthen was concentrated under a stream of nitrogen
  2. dissolutionThe residue was dissolved in water (0.2 mL)
  3. custommethanol (0.8 mL) before being purified by MDAP (modifier: formic acid)

Sources & evidence

ORD record
ord-796ba234df4648af893b9c50efc1c87b
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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