Trifluoroacetic acid → (1S,9S)-9-(benzyloxycarbonylamino)-6,10-dioxo octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

HRID 709372Notes

Reaction equation

HRID 709372 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:18](=[O:19])[N:17]2[C@H:20]([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:18](=[O:19])[N:17]2[C@H:20]([C:24]([OH:26])=[O:25])[CH2:21][CH2:22][CH2:23][N:16]2[C:15](=[O:31])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67022104(1S,9S)-tert-butyl 9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

Product 1

HCID 18396550(1S,9S)-9-(benzyloxycarbonylamino)-6,10-dioxo octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, (1S,9S)-tert-butyl 9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate (1.3 g, 3.01 mmol) was combined with CH2Cl2 (5 ml) to give a colorless solution. TFA (3.53 g, 2.38 ml, 31.0 mmol) was added and stirred at room temperature for 5 hr. The crude reaction mixture was concentrated in vacuo and redissolved in EtOAc (10 ml). It was evaporated to afford (1S,9S)-9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid as a foaming solid (1.0 g, 88.4%).

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionredissolved in EtOAc (10 ml)
  5. customIt was evaporated

Sources & evidence

ORD record
ord-56b04bdce40247dd91eedf25a7a21c90
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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