تفاعل #657346

معادلة التفاعل

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

المذيبات

1,2-DCE

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةbefore being cooled
3. 3
   ترشيحfiltered
4. 4
   غسيلThe solid was washed with DCM
5. 5
   غسيلthe filtrate washed with sat. NaHCO3
6. 6
   تجفيفThe organic layer was dried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe title compound was precipitated from a DCM/i-Pr2O mixture
10. 10
    ترشيحfiltered
11. 11
    تركيزThe filtrate was then concentrated
12. 12
    أخرىpurified by flash chromatography (DCM/MeOH: 98/2)
13. 13
    أخرىto afford another batch of product

الإجراء التجريبي

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.

المصدر