Potassium Carbonate → Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate

HRID 899916Notes

Reaction equation

HRID 899916 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[C:15]([NH:22][CH2:23][CH2:24][CH2:25][NH2:26])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:18]([O:17][C:15]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 67235341Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-fluoro-4-nitrobenzoate (5.8 g, 1 eq), N-Boc-1,3-diaminopropane (5.75 g, 1.1 eq) and potassium carbonate (8.04 g, 2 eq) in acetonitrile (200 ml) is heated under reflux for 2 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (100 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. The solid obtained is washed with petroleum ether and dried (10.2 g; 99% yield).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. concentrationthen concentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customThe solid obtained
  9. washis washed with petroleum ether
  10. customdried (10.2 g; 99% yield)

Sources & evidence

ORD record
ord-25a7aebce0b44907bc08865174e05ada
Source dataset
uspto-grants-2008_04
Patent number
US07355052B2

Reaction notes

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