Reaction #3710

Reaction equation

ethyl acetate methylene chloride

10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

triethylamine

isobutylchloroformate

→

10,11-Dihydro-10-[4-[(3-methylpropyloxycarbonyl)amino]benzoyl]-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Solvents

methylene chloride

Conditions

Workup

1. 1
   Otherquenched with 1N NaOH
2. 2
   OtherThe organic layer is evaporated in vacuo to a residue which
3. 3
   workup.STIRRINGis stirred in 5 ml of tetrahydrofuran for 1 hour
4. 4
   Otherevaporated in vacuo to a residue
5. 5
   ExtractionThe residue is extracted with ethyl acetate-methylene chloride
6. 6
   Washwashed with brine
7. 7
   Dryingdried (Na2SO4)
8. 8
   Filtrationfiltered through hydrous magnesium silicate
9. 9
   Otherevaporated in vacuo
10. 10
    Otherto give a residue which
11. 11
    Otherto give 0.22 g of cream

Procedure

To a stirred solution of 0.15 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 0.10 g of triethylamine followed by 0.10 g of isobutylchloroformate. The reaction mixture is stirred for 3 hours and then quenched with 1N NaOH. The organic layer is evaporated in vacuo to a residue which is stirred in 5 ml of tetrahydrofuran for 1 hour, then evaporated in vacuo to a residue. The residue is extracted with ethyl acetate-methylene chloride, washed with brine, dried (Na2SO4), filtered through hydrous magnesium silicate and evaporated in vacuo to give a residue which is stirred with ethyl acetate-methylene chloride to give 0.22 g of cream colored solid. MS(CI): 404 (M+H).

Source