Triethylamine → methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate

HRID 354491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 354491
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:13][CH:12]=1.[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH2:48])[CH3:47])[C:37]([O:39][CH3:40])=[O:38].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH:48][C:18](=[O:20])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:32])=[CH:16][CH:15]=1)[CH3:47])[C:37]([O:39][CH3:40])=[O:38]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 23512272pentafluorophenyl 4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587793methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate

Produkt 1

HCID 86587792methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (508 mg, 1.13 mmol), methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate (275 mg, 1.13 mmol) and Et3N (0.240 mL, 1.72 mmol) in DMF (10 mL) was stirred at room temp overnight. The mixture was diluted with EtOAc, and the solution was washed with 0.5 N HCl, sat. NaHCO3, brine, dried over Na2SO4, and evaporated. The residue was recrystallized from MeOH—CHCl3-n-hexane to give 240 mg (42%) methyl (S)-3-chloro-4-[2-[4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as a white crystalline powder. 1H-NMR (DMSO-d6) δ1.21 (d, 3H, J=6.4 Hz), 2.25 (s, 3 H), 3.33 (s, 2 H), 3.82 (s, 3 H), 4.04-4.14 (m, 3H), 6.90-6.94 (m, 1H), 7.11-7.16 (m, 4H), 7.29-7.38 (m, 3H), 7.83-7.94 (m, 3H), 8.13-8.17 (m, 2H), 9.34 (s, 1 H); MS(FAB) m/z 510 (M30).

Aufarbeitung

  1. washthe solution was washed with 0.5 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was recrystallized from MeOH—CHCl3-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b6d759512e9747b5aac11493f0a3174f
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756378B2

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