Diisopropylethylamine → N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester

HRID 895921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895921
Cl.[CH3:2][O:3][C:4](=[O:27])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:26])[N:16]([CH3:25])[C:17]([CH3:24])=[CH:18][C:19]=2[C:20]([F:23])([F:22])[F:21])=[CH:10][CH:9]=1)[NH2:6].CCN([CH:34]([CH3:36])[CH3:35])C(C)C>ClCCl>[CH3:2][O:3][C:4](=[O:27])[C@H:5]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:26])[N:16]([CH3:25])[C:17]([CH3:24])=[CH:18][C:19]=2[C:20]([F:21])([F:22])[F:23])=[CH:12][CH:13]=1)[NH:6][C:15]([C:14]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:36]=1[CH2:34][CH3:35])=[O:26]

Komponenten

4

Edukt 2

HCID 81531DiisopropylethylamineHCID 697160064-[1,6-Dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-phenylalanine methyl ester hydrochloride

Produkt 1

HCID 69715914N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl esterAusbeute 122,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the above prepared acid chloride, 4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-phenylalanine methyl ester hydrochloride (100 mg, 0.25 mmol) in dichloromethane (5 mL) was treated with DIPEA (0.17 mL, 1.0 mmol) and the resulting light brown solution was stirred for 3 days. The mixture was concentrated, diluted with ethyl acetate, washed with 1 N HCl and brine solution and was dried over magnesium sulfate. Filtration and evaporation afforded a residue, which was purified by silica gel chromatography using a Biotage column (40 s) to give N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester as a white foam (79 mg, 62%). ES-HRMS m/e calcd for C28H29F3NO4 (M+Na) 537.1974. found 537.1972. d. Preparation of N-[(2-ethyl-6-methylphenyl)carbonyl]-4-[1,6-dimethyl-4-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine

Aufarbeitung

  1. additionA mixture of the
  2. concentrationThe mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 1 N HCl and brine solution
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationFiltration and evaporation
  7. customafforded a residue, which
  8. customwas purified by silica gel chromatography
  9. customa Biotage column (40 s)

Quellen und Nachweise

ORD-Eintrag
ord-88090dbd8f7b401c96311180fa6f418a
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06916933B2

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