反応 #657345

反応方程式

Et3N

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

AcCl

hydrazine monohydrate

→

crude title compound

収率 100.0%

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

収率 100.0%

溶媒

THF

反応条件

後処理

1. 1
   その他at 0° C.
2. 2
   温度to warm to RT
3. 3
   workup.STIRRINGstir for 1 h
4. 4
   その他then quenched with water
5. 5
   濃縮concentrated under reduced pressure
6. 6
   抽出The resulting aqueous layer was then extracted with DCM
7. 7
   乾燥the organic layer was dried over Na2SO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo

実験手順

To a suspension of methyl[(3S)-5-(4-chlorophenyl)-7-(methyloxy)-2-thioxo-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]acetate (for a preparation see Intermediate 4) (30.2 g, 77.7 mmol) in THF (800 mL) at 0° C. was added hydrazine monohydrate (11.3 mL, 233 mmol) dropwise. The reaction mixture was stirred for 4 h between 0° C. and 15° C. before being cooled at 0° C. Et3N (32.4 mL, 230 mmol) was then added slowly and AcCl (16.3 mL, 230 mmol) was added dropwise. The mixture was allowed to warm to RT and stir for 1 h then quenched with water and concentrated under reduced pressure. The resulting aqueous layer was then extracted with DCM and the organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude title compound (34 g, 100% yield) which was used without further purification. LC/MS: m/z 429 [M(35Cl)+H]+, Rt 2.83 min.

出典