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

HRID 1971662Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:37])[C:18]([N:20]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]#[C:27][C:28]3[S:32][CH:31]=[N:30][CH:29]=3)=[O:19])[CH:9]2[C:12]([O:14]CC)=[O:13])=[CH:4][C:3]=1[O:38][CH3:39].[OH-].[K+]>O1CCOCC1.O.Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17](=[O:37])[C:18]([N:20]([C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]#[C:27][C:28]3[S:32][CH:31]=[N:30][CH:29]=3)=[O:19])[CH:9]2[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:38][CH3:39]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 293 mg of 8c in 3 ml of dioxane was mixed with a solution of 100 mg of KOH in 1 ml of water and stirred at 55° C. for 1 hr. After this period all ester had disappeared according to TLC. The reaction mixture was cooled, diluted with 10 ml of water and cold 0.5N HCl was added until pH 3. The product was extracted into ethyl acetate. The combined organic layers were once washed with water, dried and concentrated. The amorphous product 8d thus obtained was used without further purification in the next step.

Workup

temperatureThe reaction mixture was cooled
additionwas added until pH 3
extractionThe product was extracted into ethyl acetate
washThe combined organic layers were once washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-83efa6dfe2b74afaac0a560768a6229c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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