Hydrochloric Acid → 2-(Tert-butyl-(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetic acid
Reaction equation
[C:1]([N:5]([CH2:13][CH2:14][O:15][CH2:16][C:17]#[C:18][C:19]1[S:23][CH:22]=[N:21][CH:20]=1)[C:6](=[O:12])[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O>[C:1]([N:5]([CH2:13][CH2:14][O:15][CH2:16][C:17]#[C:18][C:19]1[S:23][CH:22]=[N:21][CH:20]=1)[C:6](=[O:12])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
A solution of 450 mg of 11e in 4 ml of dioxane was mixed with a solution of 250 mg of KOH in 2 ml of water and stirred at 55° C. for 1 h. The reaction mixture was then cooled and diluted with 20 ml of water and made acidic to pH3 by addition of 0.5N HCl. The product was extracted with ethyl acetate. The organic extract was washed once with water, dried and concentrated, to give 430 mg of 11f as a colorless oil, which solidified on standing; Mp: 104-105° C.; Rf 0.20 (CH2Cl2/methanol 8/2). MS-ESI:
Workup
- temperatureThe reaction mixture was then cooled
- extractionThe product was extracted with ethyl acetate
- extractionThe organic extract
- washwas washed once with water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-621bc18995544258bd6561c06d149bd1
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431564B2
Reaction notes
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