Sodium Hydroxide → HCID 67196448, compound

HRID 2366971Notes

Reaction equation

HRID 2366971 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]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].[OH-].[Na+].CS(C)=O.CC#N>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]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22251437Acetonitrile dimethylsulfoxideHCID 67194868HCID 67194868, compound

Product 1

HCID 67196448HCID 67196448, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoate (for a preparation see Intermediate 108) (20 mg, 0.046 mmol) in ethanol (0.5 mL) was treated with NaOH (1M in water, 0.182 mL, 0.182 mmol) and the resulting mixture was stirred at room temperature for 30 min. It was then made up to 0.9 mL by addition of 1:1 solvent mixture of DMSO/CH3CN and purified by MDAP to give 4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-3-methylbenzoic acid (16 mg, 0.038 mmol, 83%) as a white solid. LCMS (method A): Retention time 0.91 min, [M+H]+=425.18

Workup

  1. custompurified by MDAP

Sources & evidence

ORD record
ord-69593c1783d145e885f4318803765295
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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