Diethyl Ether → Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylate

HRID 1037962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037962
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][Si](C=[N+]=[N-])(C)C.CCOCC>CO.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[S:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:15]=1)[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

Produkt 1

HCID 67397774Methyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)thiazole-5-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (1.03 g, 3.8 mmol) in a mixture of MeOH (20 mL) and toluene (20 mL) cooled to 0° C. was added dropwise 2.0M trimethylsilyldiazomethane in ether (12 mL, 24 mmol). The resulting reaction mixture was warmed to room temperature overnight. Excess trimethylsilyldiazomethane was quenched with the addition of acetic acid and the solution concentrated to dryness. The residue was partitioned between EtOAc and saturated aqueous NaHCO3, the organic layer dried over anhydrous Mg2SO4 and concentrated to afford a yellow oil (0.90 g, 83%). LC-MS: (FA) ES+ 287.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to room temperature overnight
  3. customExcess trimethylsilyldiazomethane was quenched with the addition of acetic acid
  4. concentrationthe solution concentrated to dryness
  5. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  6. dry with materialthe organic layer dried over anhydrous Mg2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-09f7bb4446ae4e9d98bb247ad65d9738
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546588B2

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