Potassium Carbonate → HCID 67236483, compound

HRID 1521690Notes

Reaction equation

HRID 1521690 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[NH2:21][C:22]([CH3:27])([CH3:26])[CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:25][CH2:24][CH2:23][C:22]([NH:21][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6410003-Amino-3-methylbutan-1-olHCID 17985978HCID 17985978, compound

Product 1

HCID 67236483HCID 67236483, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of benzyl 3-fluoro-4-nitrobenzoate (2.67 g, 9.69 mmol) and 3-amino-3-methylbutan-1-ol (1.00 g, 9.69 mmol) in acetonitrile (20 mL) containing potassium carbonate (1.34 g, 9.69 mmol) is heated to 80° C. for 16 h. The solvent is evaporated, water (100 mL) is added, and the mixture is extracted with EtOAc (3×100 mL). The combined organic layers are dried (MgSO4), concentrated and purified by flash chromatography in heptanes/EtOAc to afford the title compound (395 mg, 1.10 mmol).

Workup

  1. customThe solvent is evaporated
  2. additionwater (100 mL) is added
  3. extractionthe mixture is extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography in heptanes/EtOAc

Sources & evidence

ORD record
ord-0d16e004fba842c88e96ca0e5df831a8
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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