Reacción #91480

ord-6548f0433bdd4c3c9ebe2ed0cfadbf32

Ecuación de reacción

N#Cc1ccccc1
Benzonitrile
N[C@@H](CS)C(=O)O
L-cysteine
O=P([O-])([O-])[O-]
phosphate
O=C(O)C1CSC(c2ccccc2)=N1
2-phenyl-4,5-dihydrothiazole-4-carboxylic acid
O=C(O)C1CSC(c2ccccc2)=N1
2-Phenyl-4,5-dihydrothiazole-4-carboxylic acid

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Temperatura
40°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe precipitate was removed by filtration, and MeOH
  2. 2
    Otrowas removed
  3. 3
    Otroevaporation
  4. 4
    workup.ADDITIONTo the remaining solution was added 1M HCl
  5. 5
    Otroto adjust to pH=2 under 0° C
  6. 6
    FiltraciónThe resulting precipitate was filtered

Procedimiento

Benzonitrile (40 mmol) was combined with L-cysteine (45 mmol) in 100 mL of 1:1 MeOH/pH 6.4 phosphate buffer solution. The reaction was stirred at 40° C. for 3 days. The precipitate was removed by filtration, and MeOH was removed using rotary evaporation. To the remaining solution was added 1M HCl to adjust to pH=2 under 0° C. The resulting precipitate was filtered to yield a white solid 2-phenyl-4,5-dihydrothiazole-4-carboxylic acid 42a, which was used directly to next step without purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09447049B2uspto-grants-2016_09