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

HRID 20941

Reaktionsgleichung

Reaktionsgleichung von HRID 20941
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]

Komponenten

9

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f25d641a01ff4f0589ae2ceffe2cc078
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745470B2

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