Triethylamine → Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected

HRID 2111674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111674
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]#[CH:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C1COCC1>[CH2:2]([O:3][C:4]([C:6]1[CH:20]=[C:19]([CH2:18][NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[O:8][N:7]=1)=[O:5])[CH3:1]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Produkt 1

HCID 10588096Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protectedAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of ethyl chlorooximidoacetate (10 g, 66 mmol) in THF (200 ml) was added dropwise over 3 hours to a mixture of N-(tert-butyloxycarbonyl)propargylamine (20.5 g, 131 mmol) and triethylamine (11.2 ml, 80 mmol) in tetrahyrofuran (100 ml). The mixture was stirred at ambient temperature for 18 hours and then the volatiles were removed by evaporation. The residue was dissolved in DCM and washed with water followed by brine. The organics were separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with isohexane/diethyl ether (80:20 then 50:50) to give the title compound (10.6 g, 60%). NMR (DMSO): 1.3 (t, 3H), 1.38 (s, 9H), 4.35 (m, 2H), 6.62 (s, 1H), 7.55 (s, 1H); m/z 269 (M−H)—.

Aufarbeitung

  1. customthe volatiles were removed by evaporation
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed with water
  4. customThe organics were separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography on silica gel eluting with isohexane/diethyl ether (80:20

Quellen und Nachweise

ORD-Eintrag
ord-7f84297867654b40b98f3ebe1f43cae8
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521453B2

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