反応 #657346

反応方程式

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

溶媒

1,2-DCE

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度before being cooled
3. 3
   ろ過filtered
4. 4
   洗浄The solid was washed with DCM
5. 5
   洗浄the filtrate washed with sat. NaHCO3
6. 6
   乾燥The organic layer was dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated under reduced pressure
9. 9
   その他The title compound was precipitated from a DCM/i-Pr2O mixture
10. 10
    ろ過filtered
11. 11
    濃縮The filtrate was then concentrated
12. 12
    その他purified by flash chromatography (DCM/MeOH: 98/2)
13. 13
    その他to afford another batch of product

実験手順

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.

出典