HCID 53757969, compound → HCID 54232542, compound

HRID 850900Notes

Reaction equation

HRID 850900 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:5]2[C@@H:4]2[CH2:23][CH2:24][N:3]12>FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([OH:18])=[O:17])=[C:5]2[C@@H:4]2[CH2:23][CH2:24][N:3]12

Participants

3

Reactant 1

HCID 53757969HCID 53757969, compound

Product 1

HCID 54232542HCID 54232542, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.77 g (5.4 mmol) of t-butyl (S)-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo [1,5-a][1,4]benzodiazepine-1-carboxylate are stirred in 14 ml of trifluoroacetic acid at 50° for 3 hours and at 65° for 3.5 hours. Subsequently, the mixture is evaporated to dryness and the residue is heated on a steam-bath for 2.5 hours in a high vacuum. The material is treated with ether, stirred for 1 hour while cooling with ice, the solid material is filtered off under suction while back-washing with ether and then dried. There is obtained (S)-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid of melting point 232°.

Workup

  1. customSubsequently, the mixture is evaporated to dryness
  2. temperaturethe residue is heated on a steam-bath for 2.5 hours in a high vacuum
  3. additionThe material is treated with ether
  4. temperaturewhile cooling with ice
  5. filtrationthe solid material is filtered off under suction
  6. washwhile back-washing with ether
  7. customdried

Sources & evidence

ORD record
ord-17ec2ee7b1f64898b2cd909820583e04
Source dataset
uspto-grants-1983_05
Patent number
US04382032

Reaction notes

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