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

HRID 1954057Notes

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>C(Cl)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 methylene 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-84c068f9e38c4c26ad05218f5536aa60
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121258

Reaction notes

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