Sodium Hydroxide → 4-(4-But-2-ynyloxybenzenesulfonyl)-1-(pyrrolidine-1-carbonyl)-piperidine-4-carboxylic acid

HRID 278352Notes

Reaction equation

HRID 278352 reaction equation
C[O:2][C:3]([C:5]1([S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]#[C:30][CH3:31])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:10][CH2:9][N:8]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1.CO>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([C:5]2([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][N:8]([C:11]([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)=[O:12])[CH2:9][CH2:10]2)(=[O:20])=[O:19])=[CH:26][CH:25]=1)[C:29]#[C:30][CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 539416784-(4-but-2-ynyloxybenzenesulfonyl)-1-(pyrrolidine-1-carbonyl)-piperidine-4-carboxylic Acid Methyl Ester

Product 1

HCID 235138364-(4-But-2-ynyloxybenzenesulfonyl)-1-(pyrrolidine-1-carbonyl)-piperidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

4-(4-But-2-ynyloxybenzenesulfonyl)-1-(pyrrolidine-1-carbonyl)-piperidine-4-carboxylic acid was prepared following the procedure of Example 64 (step 5). Starting from 4-(4-but-2-ynyloxybenzenesulfonyl)-1-(pyrrolidine-1-carbonyl)-piperidine-4-carboxylic acid methyl ester (250 mg, 0.52 mmol) in 4 ml of tetrahydrofuran:methanol (1:1) and 1N sodium hydroxide (1.03 ml, 1.03 mmol), 150 mg of (62%) of the acid was isolated. HR-MS: m/z Calculated for C24H25NO7S 472.1425; Found 472.1426.

Workup

  1. customwas isolated

Sources & evidence

ORD record
ord-b17e1c545030403f99d828a6aabf9f77
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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