4-Methylmorpholine → tert-butyl N-{4'-[3-(N'-butyrylhydrazino)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylcarbamate

HRID 730408

Reaktionsgleichung

Reaktionsgleichung von HRID 730408
[CH3:1]N1CCOCC1.C(OC([CH2:15][NH:16][CH2:17][C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH:31]([O:35][CH2:36][CH3:37])[C:32](O)=[O:33])=[CH:26][CH:25]=2)[CH:21]=[CH:22][CH:23]=1)=O)(C)(C)C.[C:38]([NH:43][NH2:44])(=[O:42])[CH2:39][CH2:40][CH3:41].ON1C2C=C[CH:53]=[CH:54][C:49]=2N=N1.C(N=C=NC(C)C)(C)C.[C:64]([O:67]CC)(=[O:66])C>O1CCCC1>[C:38]([NH:43][NH:44][C:32](=[O:33])[CH:31]([O:35][CH2:36][CH3:37])[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][N:16]([CH3:15])[C:64](=[O:66])[O:67][C:54]([CH3:53])([CH3:49])[CH3:1])[CH:19]=2)=[CH:25][CH:26]=1)(=[O:42])[CH2:39][CH2:40][CH3:41]

Komponenten

8

Edukt 6

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77079ButyrohydrazideHCID 688520833-{3'-[(Tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionic acid

Produkt 1

HCID 68852131tert-butyl N-{4'-[3-(N'-butyrylhydrazino)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylcarbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

0.15 ml (1.33 mmol) of N-methylmorpholine is added to a solution of 0.5 g (1.2 mmol) of 3-{3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionic acid, 0.14 g (1.3 mmol) of butyric hydrazide and 0.33 g (2.4 mmol) of 1-hydroxybenzotriazole in 10 ml of tetrahydrofuran cooled to −5° C. After stirring for 5 minutes, 0.2 ml (1.3 mmol) of diisopropylcarbodiimide is added. The reaction medium is stirred at 0° C. for 1 hour and then at room temperature for 2 hours, diluted with ethyl acetate, washed with saturated aqueous caesium hydrogen carbonate solution, extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. The residue obtained is chromatographed on a column of silica eluted with a 1/1 heptane/ethyl acetate mixture. 0.6 g of tert-butyl N-{4′-[3-(N′-butyrylhydrazino)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylcarbamate is obtained in a yield of 100%.

Aufarbeitung

  1. stirringThe reaction medium is stirred at 0° C. for 1 hour
  2. waitat room temperature for 2 hours
  3. washwashed with saturated aqueous caesium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customis chromatographed on a column of silica
  10. washeluted with a 1/1 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-232fb9bc676e4d25827e2f4eb22ebbce
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582663B2

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