Sodium Hydroxide → 4-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoic acid

HRID 2041780Notes

Reaction equation

HRID 2041780 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][C:15]=3[CH3:24])=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:6][C@@H:5]1[CH3:32])(=[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][C:15]=3[CH3:24])=[CH:11][CH:12]=2)[C@H:7]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67206073Methyl 4-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate

Product 1

HCID 672065004-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoic acidYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate (for a preparation see Example 173) (25 mg, 0.058 mmol) was dissolved in ethanol (1 mL) and treated with sodium hydroxide (1M in water, 0.291 mL, 0.291 mmol) and the resulting mixture was stirred at room temperature for 4 h then was concentrated in vacuo. Purification of the residue by MDAP (modifier: formic acid) gave 4-[(2S,4R)-1-acetyl-2-methyl-4-(3-pyridinylamino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoic acid (2 mg, 8%) as a brown solid.

Workup

  1. concentrationthen was concentrated in vacuo
  2. customPurification of the residue by MDAP (modifier: formic acid)

Sources & evidence

ORD record
ord-27bded564e514b628b7b13d6580561d1
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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