Hydrochloric Acid → HCID 58124897, compound

HRID 1971725Notes

Reaction equation

HRID 1971725 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][CH2:23][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]([CH3:34])([CH3:35])[CH3:33])[CH2:21][CH2:22][CH2:23][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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124843Ethyl 7-bromo-2-(2-(tert-butyl(6-(thiazol-5-yl)hex-5-ynyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Product 1

HCID 58124897HCID 58124897, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 300 mg of 17g in 3 ml of dioxane was mixed with 130 mg of KOH in 1 ml of water. The mixture was stirred at 50° C. for 1.5 hr, cooled, diluted with 20 ml of water, acidified to pH3 (0.2N HCl) and extracted with ethyl acetate. The extract was washed twice with water, dried and concentrated, to give 240 mg of acid 17h as a colorless foam.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed twice with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b1ab5b5208444a5b4940ccdd0683ab8
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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