Hydrochloric Acid → HCID 19070811, compound

HRID 1955599Notes

Reaction equation

HRID 1955599 reaction equation
[CH:1]1([C:4]([CH2:6][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][C:19]([CH:21]3[CH2:23][CH2:22]3)=[O:20])[C:10](=[O:24])[CH:9]([NH:25]C(OC(C)(C)C)=O)[C:8]2=[O:33])=[O:5])[CH2:3][CH2:2]1.Cl>C(OCC)(=O)C>[CH:21]1([C:19]([CH2:18][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([CH2:6][C:4]([CH:1]3[CH2:2][CH2:3]3)=[O:5])[C:8](=[O:33])[CH:9]([NH2:25])[C:10]2=[O:24])=[O:20])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19070823HCID 19070823, compound

Product 1

HCID 19070811HCID 19070811, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of previously prepared 1,5-bis-(cyclopropylcarbonylmethyl)-3-(t-butoxycarbonylamino)-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 14 h (3.188 g) in ethyl acetate (16 ml) is added a solution of 4N HCl in ethyl acetate (14 ml) under ice-cooling. After stirring the reaction mixture for 15 hr at room temperature, crystalline preparations are filtered off. The resultant crystals are dissolved into methylene chloride/methanol (5:1) and washed with saturated aqueous sodium hydrogencarbonate solution. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure. Crystallization from a mixture of methylene chloride, methanol and diisopropyl ether yields the titled Compound 16 h (2.092 g; yield, 84%).

Workup

  1. temperaturecooling
  2. filtrationcrystalline preparations are filtered off
  3. dissolutionThe resultant crystals are dissolved into methylene chloride/methanol (5:1)
  4. washwashed with saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customCrystallization
  8. additionfrom a mixture of methylene chloride, methanol and diisopropyl ether
  9. customyields

Sources & evidence

ORD record
ord-e7cdda0bd3934eafaeee62808ccbecc8
Source dataset
uspto-grants-1998_07
Patent number
US05776929

Reaction notes

Loading…