Hydrochloric Acid → HCID 54560925, compound

HRID 369552Notes

Reaction equation

HRID 369552 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C@H:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:13]([N:26]([CH3:28])[CH3:27])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[N+:29]([O-])([O-:31])=[O:30].[Na+].Cl.CC(OC(C)=O)=O>C(OC(=O)C)(=O)C.CCOCC.ClCCl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([N:26]([CH3:28])[CH3:27])[C:14]([O:17][C@H:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:16]=2[N+:29]([O-:31])=[O:30])=[CH:7][CH:6]=1)=[O:4]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7918Acetic AnhydrideHCID 24268Sodium NitrateHCID 54555941HCID 54555941, compound

Product 1

HCID 54560925HCID 54560925, compoundYield 43.1%

Reagents, catalysts & solvents 4

HCID 7918Acetic AnhydrideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (3 drops) was added to a stirred solution of compound 63 (75 mg, 0.195 mmol), sodium nitrate (17 mg, 0.205 mmol), water (0.3 ml), concentrated HCl (0.16 ml), dichloromethane (0.5 ml), and ether (3 ml). The reaction mixture was stirred for 15 minutes and then more HCl and Ac2O were added until the solution changed color to a bright yellow. After the color had changed, the reaction mixture was stirred for an additional three hours, and then the organic layer was separated, washed with brine, and dried over MgSO4. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc). Evaporation of solvent yielded 36 mg (43%) of a yellow solid.

Workup

  1. stirringthe reaction mixture was stirred for an additional three hours
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-80/20 (Hex/EtOAc)
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-010eb0073a0e4188b3ac0f0dda093917
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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