Hydrochloric Acid → 2-((2-(Tert-butoxycarbonyl(3-(thiophen-2-yl)prop-2-ynyl)amino)ethyl)(isopropyl)amino)-2-oxoacetic acid

HRID 1971678Notes

Reaction equation

HRID 1971678 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]#[C:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[C:13]([O:15]CC)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]#[C:24][C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[C:13]([OH:15])=[O:14])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124877Ethyl 2-((2-(tert-butoxycarbonyl(3-(thiophen-2-yl)prop-2-ynyl)amino)ethyl)-(isopropyl)amino)-2-oxoacetate

Product 1

HCID 581248782-((2-(Tert-butoxycarbonyl(3-(thiophen-2-yl)prop-2-ynyl)amino)ethyl)(isopropyl)amino)-2-oxoacetic acidYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 400 mg of 10h in 6 ml of dioxane was mixed with a solution of 180 mg of KOH in 1.5 ml of water and stirred for 2 hr at RT. The reaction mixture was diluted with 20 ml of water and acidified to pH3 by addition of 0.5N HCl. The product was extracted into ethyl acetate. The combined organic layers were once washed with water, dried and concentrated, to provide 320 mg of 10i as colorless oil:

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washThe combined organic layers were once washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3350fd1048364417a197276f517058ed
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…