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

HRID 709356Notes

Reaction equation

HRID 709356 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[N:11]2[C@H:14]([C:18]([O:20]C(C)(C)C)=[O:19])[CH2:15][CH2:16][CH2:17][N:10]2[C:9](=[O:25])[CH2:8][CH2:7]1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[N:11]2[C@H:14]([C:18]([OH:20])=[O:19])[CH2:15][CH2:16][CH2:17][N:10]2[C:9](=[O:25])[CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70663762(1S,9S)-tert-butyl 9-(methoxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

Product 1

HCID 70663807(1S,9S)-9-(methoxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,9S)-tert-butyl 9-(methoxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate (1.25 g, 3.52 mmol) dissolved into methylene chloride (10 mL) was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 1 h and concentrated in vacuo. Toluene (5 mL) was added and the reaction concentrated in vacuo to afford (1S,9S)-9-(methoxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid as a white solid, (587 mg, 68%): ESI-LRMS m/e calcd for C12H17N3O6[M+] 299. found 300 [M+H+].

Workup

  1. concentrationconcentrated in vacuo
  2. additionToluene (5 mL) was added
  3. concentrationthe reaction concentrated in vacuo

Sources & evidence

ORD record
ord-e861f29262f44581aa78b327d6ce4f19
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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