Reacción #657346

Ecuación de reacción

P4S10

Na2CO3

methyl[(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate

→

title compound

Methyl[(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-thioxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate

Disolventes

1,2-DCE

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturabefore being cooled
3. 3
   Filtraciónfiltered
4. 4
   LavadoThe solid was washed with DCM
5. 5
   Lavadothe filtrate washed with sat. NaHCO3
6. 6
   SecadoThe organic layer was dried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe title compound was precipitated from a DCM/i-Pr2O mixture
10. 10
    Filtraciónfiltered
11. 11
    ConcentraciónThe filtrate was then concentrated
12. 12
    Otropurified by flash chromatography (DCM/MeOH: 98/2)
13. 13
    Otroto afford another batch of product

Procedimiento

A suspension of P4S10 (85.8 g, 190 mmol) and Na2CO3 (20.5 g, 190 mmol) in 1,2-DCE (1.5 L) at RT was stirred for 1 h before methyl[(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate (for a preparation see Intermediate 5) (40 g, 107 mmol) was added. The resulting mixture was stirred at 65° C. for 4 h before being cooled and filtered. The solid was washed with DCM and the filtrate washed with sat. NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The title compound was precipitated from a DCM/i-Pr2O mixture and filtered. The filtrate was then concentrated and purified by flash chromatography (DCM/MeOH: 98/2) to afford another batch of product. The title compound was obtained combining the two fractions (30.2 g, 73%) as a yellow powder. LC/MS: m/z 389 [M(35Cl)+H]+, Rt 3.29 min.

Fuente