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

HRID 20941

반응식

HRID 20941 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f25d641a01ff4f0589ae2ceffe2cc078
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745470B2

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