Trifluoroacetic acid → 1,5-Di-[(4methoxyphenyl)sulfonyl]-diazepine-2-carboxylic acid

HRID 2184786Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:15][CH2:14][N:13]2[C:30]([O:32]C(C)(C)C)=[O:31])(=[O:11])=[O:10])=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>[Cl-]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:15][CH2:14][N:13]2[C:30]([OH:32])=[O:31])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The t-butyl 1,5-di-[(4-methoxyphenyl)sulfonyl]-diazepine-2-carboxylate (0.45 g, 0.8 mmol) is dissolved in chloride (1.5 mL) and cooled down in an ice bath. Trifluoroacetic acid (1.5 mL, 19.0 mmol is added and the resulting solution is stirred at 0° C. for 3 hours. The reaction mixture is warmed to room temperature and an additional 1 mL of trifluroacetic acid is added. The resulting solution is stirred for an additional hour and the mixture is concentrated under reduced pressure. The residue is carried forward without further purification. MS (ESI): 485 (M+H+), 502 (M+NH4+).

Workup

temperaturecooled down in an ice bath
temperatureThe reaction mixture is warmed to room temperature
stirringThe resulting solution is stirred for an additional hour
concentrationthe mixture is concentrated under reduced pressure
customThe residue is carried forward without further purification

Sources & evidence

ORD record: ord-0464ac2c55fe4cb58f6b9b25457e1bc6
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399598B1

Reaction notes

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