Calcium Carbonate → 2-(tert-Butoxycarbonylaminomethyl)-4-methylthiazole-5-carboxylic acid ethyl ester

HRID 1376616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376616
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[S:12])[NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Ca+2]>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:12][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[N:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 10112Calcium CarbonateHCID 11858Ethyl 2-chloroacetoacetateHCID 5324304tert-butyl N-(carbamothioylmethyl)carbamate

Produkt 1

HCID 229166822-(tert-Butoxycarbonylaminomethyl)-4-methylthiazole-5-carboxylic acid ethyl esterAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 5.02 g of (tert-butoxycarbonylamino)acetothioamide in 75 ml of ethanol were added 3.92 ml of ethyl 2-chloroacetoacetate and 2.75 g of calcium carbonate, and the mixture was stirred at 50° C. for 6 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with a 5:1 mixture of toluene and ethyl acetate to give 5.65 g (yield 71%) of the title compound.

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with a 5:1 mixture of toluene and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2abacfe40f3c4aa187382bbd926eb771
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663162

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