Triethylamine → HCID 67282364, compound

HRID 1616175Notes

Reaction equation

HRID 1616175 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)=[O:4].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.[C:39]([NH2:48])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40]>O.CN(C=O)C>[N+:14]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][C:9]=1[C:10](=[O:12])[NH:48][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40])([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 149380985-(Methoxycarbonyl)-2-nitrobenzoic acid

Product 1

HCID 67282364HCID 67282364, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(methoxycarbonyl)-2-nitrobenzoic acid (0.12 g, 0.53 mmol), DMF (2.50 mL), triethylamine (0.22 mL, 1.6 mmol) and fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (0.17 g, 0.64 mmol) was stirred for 30 min and cumylamine (0.092 mL, 0.64 mmol) was added. The reaction mixture was stirred at rt for 1 d. Water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 4-nitro-3-[(2-phenylpropan-2-yl)carbamoyl]benzoate (0.13 g, 70%). LC-MS: (FA) ES+ 343.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 d
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-73757c864cce4abdb9528c11d4bc6895
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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