Ethyl Acetate → benzyl 9-chloro-5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepine-7-carbamate

HRID 354768Notes

Reaction equation

HRID 354768 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:24])[C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.C(=O)(O)[O-].[Na+].[CH2:30]([O:37][C:38](Cl)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>O1CCCC1.O>[Cl:24][C:4]1[C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:14])([CH3:15])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=[C:2]([NH:1][C:38]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 205061437-amino-9-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 20506189benzyl 9-chloro-5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepine-7-carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12 g (0.035 mol) of 7-amino-9-chloro-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one are dissolved in 360 ml of dry tetrahydrofuran, treated with 10 g of ground sodium bicarbonate and 8 ml of chloroformic acid benzyl ester and stirred at room temperature for 31/2 hours. The mixture is treated with ethyl acetate and water, and separated aqueous phase is extracted twice with ethyl acetate and the combined organic extracts are dried and evaporated. The residue is chromatographed on 600 g of silica gel with methylene chloride/ethyl acetate (20:1 ) as the elution agent. From ether there is obtained benzyl 9-chloro-5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepine-7-carbamate of melting point 212°.

Workup

  1. customseparated aqueous phase
  2. extractionis extracted twice with ethyl acetate
  3. customthe combined organic extracts are dried
  4. customevaporated
  5. customThe residue is chromatographed on 600 g of silica gel with methylene chloride/ethyl acetate (20:1 ) as the elution agent

Sources & evidence

ORD record
ord-7fb2a982a36b4fd2813bf5345aaa8e9b
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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