Hydrochloric Acid → 7-Bromo-2-(2-(tert-butyl(2-(3-(thiazol-5-yl)prop-2-ynyloxy)ethyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

HRID 1971691Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:36])[C:18]([N:20]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:27]3[S:31][CH:30]=[N:29][CH:28]=3)=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:37][CH3:38].[OH-].[K+].Cl>O1CCOCC1.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:36])[C:18]([N:20]([C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:21][CH2:22][O:23][CH2:24][C:25]#[C:26][C:27]3[S:31][CH:30]=[N:29][CH:28]=3)=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:37][CH3:38]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 500 mg of 11g in 6 ml of dioxane was mixed with a solution of 300 mg of KOH in 3 ml of water and heated to 50° C. for 2 h. The reaction mixture was cooled and diluted with water and then acidified to pH3 by addition of 0.5N HCl. The product was extracted with ethyl acetate and the organic extract was washed once with water, dried and concentrated, to provide 480 mg of 11h as colorless amorphous material;

Workup

temperatureThe reaction mixture was cooled
extractionThe product was extracted with ethyl acetate
extractionthe organic extract
washwas washed once with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-130e8e1cd569473abae248d6a7010044
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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