Hydrochloric Acid → HCID 118411577, compound

HRID 1050910Notes

Reaction equation

HRID 1050910 reaction equation
Cl.N[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)=[O:21])[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:9].N([O-])=[O:35].[Na+].Cl>O.C(#N)C.O1CCOCC1>[OH:35][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:19][C:20]([C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)=[O:21])[C:8]([NH:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:9]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 118411663HCID 118411663, compound

Product 1

HCID 118411577HCID 118411577, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

6-Amino-2-(4-phenylbenzenecarbonyl)amino-N-(4-chlorobenzyl)hexanamide hydrochloride (173) (1.29 g) was dissolved in water (50 ml) and acetonitrile (20 ml). To the solution were added sodium nitrite (4.02 g) and a solution of 4 N hydrochloric acid in 1,4-dioxane (3.31 ml) under cooling with ice, and the mixture was stirred for 1.0 hour under cooling with ice. After 1.5 hours, the reaction liquid was warmed to room temperature and stirred for 2.0 hours. The reaction liquid was concentrated and extracted with ethyl acetate (100 ml). The organic layer was washed with brine (100 ml), dried over anhydrous sodium sulfate, and filtered. After that, the filtrate was concentrated and the residue was purified by silica gel flash column chromatography (developing solvent: chloroform:methanol=100:1 to chloroform:methanol=30:1) to give a compound (175) (561 mg, yield: 47%) as a white solid. 1H NMR data on the compound (175) is shown below.

Workup

  1. temperatureunder cooling with ice
  2. waitAfter 1.5 hours
  3. customthe reaction liquid
  4. stirringstirred for 2.0 hours
  5. customThe reaction liquid
  6. concentrationwas concentrated
  7. extractionextracted with ethyl acetate (100 ml)
  8. washThe organic layer was washed with brine (100 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationAfter that, the filtrate was concentrated
  12. customthe residue was purified by silica gel flash column chromatography (developing solvent: chloroform:methanol=100:1 to chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-febf7307f6e74804abc51d807a6757e7
Source dataset
uspto-grants-2016_07
Patent number
US09388123B2

Reaction notes

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