Hydrochloric Acid → 2-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester

HRID 2075500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075500
[F:1][C:2]([F:27])([F:26])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[C:23](O)=[O:24])=[CH:7][CH:6]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[CH3:48][O:49][C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[NH2:52].Cl>O.CN(C=O)C>[CH3:48][O:49][C:50](=[O:55])[C:51]([CH3:54])([NH:52][C:23]([C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[O:12][CH2:11][C:8]1[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:27])([F:26])[F:1])=[CH:6][CH:7]=1)=[O:24])[CH3:53]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 667011311-[6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid

Produkt 1

HCID 667010892-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

At 0° C. to 115 mg 1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid in 2 mL of abs. DMF 82 mg EDC, 45 mg 1-hydroxybenzotriazole and 49 mg N,N-diisopropylethylamine were added. After 30 min at 0° C. 56 mg of 2,2-dimethylglycine methyl ester hydrochloride and 49 mg N,N-diisopropylethylamine were added. The mixture was stirred for 16 h at room temperature. The mixture was poured into cold water, acidified to pH 3 with 2M HCl, extracted with ethyl acetate, washed with sat. sodium hydrogen carbonate solution and brine, dried over magnesium sulphate, filtrated and concentrated in vacuo to provide 124 mg of 2-methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with sat. sodium hydrogen carbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d0951e4ed59841e48aa70c439ccfad2f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919628B2

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