Chloroacetone → tert-butyl [(1R)-1-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate

HRID 1099098

Reaktionsgleichung

Reaktionsgleichung von HRID 1099098
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([CH3:12])[C:9]([NH2:11])=[S:10])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:15][C:16](=O)[CH3:17]>C(O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]([C:9]1[S:10][CH:15]=[C:16]([CH3:17])[N:11]=1)[CH3:12])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 6571ChloroacetoneHCID 5324342tert-butyl [(1R)-2-amino-1-methyl-2-thioxoethyl]carbamate

Produkt 1

HCID 59216334tert-butyl [(1R)-1-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of tert-butyl[(1R)-2-amino-1-methyl-2-thioxoethyl]carbamate (100 mg, 0.49 mmol) with 3 equivalents of chloroacetone (0.135 g) in ethanol (1 mL) was heated at 80° C. for 2 h. After cooling, the solution was concentrated. The residue was dissolved in DCM (1 ml). To the solution was added TFA (1 mL). The mixture was stirred at RT for 30 min. The volatiles were removed under reduced pressure to yield desired product.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in DCM (1 ml)
  4. additionTo the solution was added TFA (1 mL)
  5. customThe volatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8da26c2187ea407e9446fd2a4484fb8a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143251B2

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