反应 #657346

反应方程式

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

溶剂

1,2-DCE

反应条件

后处理

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

实验过程

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.

来源