N-Methylbutylamine → 3-(Butyl(methyl)carbamoyl)benzoic acid

HRID 20941

Reaction equation

HRID 20941 reaction equation
C(OC(N1C[C@H](O)C[C@@H]1C(O)=O)=O)(C)(C)C.[CH2:17]([N:21]([CH3:34])[C:22]([C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29]C)=[O:28])=[O:23])[CH2:18][CH2:19][CH3:20].COC(C1C=C(C=CC=1)C(O)=O)=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNCCCC>ClCCl.CN(C=O)C>[CH2:17]([N:21]([CH3:34])[C:22]([C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([OH:29])=[O:28])=[O:23])[CH2:18][CH2:19][CH3:20]

Participants

9

Reactant 6

HCID 8068N-MethylbutylamineHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 688616N-Boc-cis-4-hydroxy-D-prolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67316285Methyl 3-(butyl(methyl)carbamoyl)benzoate

Product 1

HCID 434527753-(Butyl(methyl)carbamoyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Step F (1): Methyl 3-(butyl(methyl)carbamoyl)benzoate. To a solution of 3-(methoxycarbonyl)benzoic acid (1.8 g, 10 mmol) in dichloromethane (40 mL) and DMF (20 mL) was added Hunig's base (2.58 g, 20 mmol) to make a clear solution and HATU (4.18 g, 11 mmol) was then added. After stirring for 10 min, the reaction mixture was added methylbutylamine (1.13 g, 13 mmol) and the reaction mixture was stirred at rt for 3 h. Dichloromethane was removed and ethyl acetate (300 mL) was added and the mixture was washed with 1N HCl, sodium carbonate solution, H2O, dried and concentrated to give the title compound ready for next step without purification: 1H NMR (CDCl3, 500 MHz) δ 0.79-0.98 (3H, m), 1.15 (1H, m), 1.41 (1H, brd s), 1.52 (1H, brd s), 1.64 (1H, m), 2.92-3.07 (2H, m), 3.21 (1H, brd s), 3.53 (1H, brd s), 3.91 (3H, s), 7.47 (1H, m), 7.58 (1H, d, J=10 Hz), 8.05-8.07 (2H, m).

Workup

  1. additionwas then added
  2. stirringthe reaction mixture was stirred at rt for 3 h
  3. customDichloromethane was removed
  4. additionethyl acetate (300 mL) was added
  5. washthe mixture was washed with 1N HCl, sodium carbonate solution, H2O
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f25d641a01ff4f0589ae2ceffe2cc078
Source dataset
uspto-grants-2010_06
Patent number
US07745470B2

Linked notes

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