Lithium Hydroxide → 4-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

HRID 736752Notes

Reaction equation

HRID 736752 reaction equation
C[O:2][C:3]([CH:5]1[CH:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH2:8][N:7]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:6]1)=[O:4].[OH-].[Li+]>C1COCC1.CO.O>[C:37]([O:36][C:34]([N:7]1[CH2:8][CH2:9][CH:10]([NH:11][S:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[C:25]([CH3:33])[CH:24]=3)=[CH:19][CH:20]=2)(=[O:13])=[O:14])[CH:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 688173164-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

Product 1

HCID 688188354-[4-(2-Methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.3 g, 0.525 mmol) and lithium hydroxide (0.1 g, 4.2 mmol) in THF:methanol:water (2.5: 1.5:1.5 mL) was stirred at 25° C. for 19 h. The solution was concentrated in vacuo to provide 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester as a crude solid (0.170 g, 58%). MS: 557 (M+H)+

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-9ef39234ff5c4318a88d5d6655e2d285
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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