Water → methyl 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionate

HRID 1295290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295290
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[C:23]1([C:29]2[N:30]=[C:31]([NH:40][CH2:41][CH2:42][CH3:43])[S:32][C:33]=2[CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[H-].[Na+].O>CN(C)C=O>[CH3:14][C:13]1[O:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][N:40]([C:31]2[S:32][C:33]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:29]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:30]=2)[CH2:41][CH2:42][CH3:43])=[CH:4][CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 22930670methyl 3-[4-phenyl-2-[N-(1-propyl)amino]-5-thiazolyl]propionate

Produkt 1

HCID 69430779methyl 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (433 mg) and methyl 3-[4-phenyl-2-[N-(1-propyl)amino]-5-thiazolyl]propionate (400 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (60% in oil, 55.2 mg) at 0° C. and the mixture was stirred at said temperature for 1 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-[N-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-N-(1-propyl)amino]-4-phenyl-5-thiazolyl]propionate (595 mg, yield 78%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Aufarbeitung

  1. customfor 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92cd053877b8415f8435d1dc8d8dfbe4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241785B2

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