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

HRID 350552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350552
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([O:23]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[Cl:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH2:47][C@@H:48]([NH2:50])[CH3:49])[C:39]([O:41][CH3:42])=[O:40]>CN(C=O)C.CCOC(C)=O>[Cl:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH2:47][C@@H:48]([NH:50][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:49])[C:39]([O:41][CH3:42])=[O:40]

Komponenten

5

Edukt 2

HCID 23512249pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587793methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate

Produkt 1

HCID 86587794methyl (S)-3-chloro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoateAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (513 mg, 1.07 mmol), methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate (260 mg, 1.07 mmol) and Et3 N (220 μl, 1.58 mmol) in DMF (10 mL) was stirred at room temp overnight. The mixture was diluted with EtOAc and the solution was washed with sat. NaHCO3, dried over Na2SO4, and evaporated. The residue was recrystallized from MeOH—CHCl3-EtOAc-n-hexane to give 400 mg (69%) methyl (S)-3-chloro-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as pale brown crystalline powder. 1H-NMR (DMSO-d6) δ 1.21 (d, 3 H, J=6.4 Hz), 2.24 (s, 3 H), 3.37 (s, 2 H), 3.82(s, 3 H), 3.83 (s, 3 H), 4.04–4.12 (m, 3 H), 6.75–6.77 (m, 1 H), 6.91–6.95 (m, 2 H), 7.11–7.17 (m, 2 H), 7.29–7.31 (m, 1 H), 7.78–7.99 (m, 4 H), 8.12–8.13 (m, 1H), 8.46 (s, 1 H), 8.55 (s, 1 H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-79f60a2c70cc455988c79736508b65cd
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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