Acetic Acid → HCID 117636219, compound

HRID 1050909Notes

Reaction equation

HRID 1050909 reaction equation
N[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([NH:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19])[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].N([O-])=[O:27].[Na+].C(O)(=O)C>O.C(#N)C>[C:20]1([C:18]([NH:17][CH:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:27])[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 118411636HCID 118411636, compound

Product 1

HCID 117636219HCID 117636219, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-(N-Benzenecarbonyl)amino-6-amino-N-benzylhexanamide (105) (48 mg) obtained in Step 1-4 was dissolved in water (1.6 ml) and acetonitrile (1.1 ml). To the solution were added sodium nitrite (156 mg) and acetic acid (40.6 mg) under cooling with ice, and the mixture was stirred for 1 hour under cooling with ice. After 1 hour, the reaction liquid was warmed to room temperature and stirred for 1.5 hours. Subsequently, the reaction liquid was heated to 70° C. and stirred for an additional 20 minutes. The reaction liquid was concentrated and extracted with ethyl acetate (60 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: n-hexane:ethyl acetate=2:1 to n-hexane:ethyl acetate=1:6) to give a compound (106) (19.5 mg, yield: 41%) as a pale yellow solid. 1H NMR data on the compound (106) is shown below.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. waitAfter 1 hour
  4. customthe reaction liquid
  5. stirringstirred for 1.5 hours
  6. customSubsequently, the reaction liquid
  7. temperaturewas heated to 70° C.
  8. stirringstirred for an additional 20 minutes
  9. customThe reaction liquid
  10. concentrationwas concentrated
  11. extractionextracted with ethyl acetate (60 ml)
  12. washThe organic layer was washed with brine (100 ml)
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationAfter that, the filtrate was concentrated
  16. customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=2:1 to n-hexane:ethyl acetate=1:6)

Sources & evidence

ORD record
ord-696a80ea6a78418b8a1150c1a93b7b8b
Source dataset
uspto-grants-2016_07
Patent number
US09388123B2

Reaction notes

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