Triethylamine → 2-({(2S)-2-{[4-(Cyclopropylmethoxy)benzoyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetate

HRID 1799267

Reaktionsgleichung

Reaktionsgleichung von HRID 1799267
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:15]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:37])[C@@H:23]([NH2:36])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)(=[O:17])[CH3:16].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>C(OCC)(=O)C.CN(C=O)C>[C:15]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:37])[C@@H:23]([NH:36][C:10](=[O:12])[C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)=[CH:14][CH:13]=1)[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:27][CH:26]=1)(=[O:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 226453014-(Cyclopropylmethoxy)benzoic acidHCID 690175432-({(2S)-2-amino-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetate

Produkt 1

HCID 690173752-({(2S)-2-{[4-(Cyclopropylmethoxy)benzoyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetateAusbeute 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(Cyclopropylmethoxy)benzoic acid (1.52 g, 7.90 mmol) prepared in Example 18 (18a) was added to a DMF (53 mL) solution of 2-({(2S)-2-amino-3-[4-(trifluoromethoxy)phenyl]propanoyl}amino)ethyl acetate (2.64 g, 7.90 mmol). To the mixture was added diethyl cyanophosphate (1.54 mL, 9.78 mmol) under ice-cooling with stirring, and then triethylamine (1.32 mL, 9.78 mmol) was dropwise added thereto over 5 minutes. The resulting mixture was stirred at room temperature for 2.5 hours, and to this reaction solution was added ethyl acetate (380 mL). The resulting mixture was washed with water (380 mL, three times) and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the obtained residue was washed with ethyl acetate and dried to give 1.47 g of the title compound. The ethyl acetate used for the washing was also concentrated, and the resulting residue was washed with methanol to give 0.82 g of the title compound. These compound fractions were combined to give 2.29 g of the title compound (white powder, yield: 57%).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe resulting mixture was stirred at room temperature for 2.5 hours
  3. washThe resulting mixture was washed with water (380 mL, three times) and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. washthe obtained residue was washed with ethyl acetate
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-208e8e0feb0f48bfb129bc800930df43
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344029B2

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