Trifluoroacetic acid → HCID 22499328, compound

HRID 1815704Notes

Reaction equation

C(NC(=O)O)(C)(C)C.[CH2:9]([C:13]1([S:16]([NH2:19])(=[O:18])=[O:17])[CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12].C(O)(C(F)(F)F)=O>>[CH2:9]([C:13]1([S:16]([NH2:19])(=[O:17])=[O:18])[CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 69264897HCID 69264897, compound

Product 1

HCID 22499328HCID 22499328, compound

Procedure

Step 30b) A mixture of 1-butyl-cyclopropylsulfonylamine tert-butylcarbamate (1.2 g, 4.3 mmol) and TFA (2 mL, 26 mmol) was stirred at rt overnite. The solvent was removed in vacuo and the residue was chromatographed over SiO2 eluting with EtOAC/Hexanes (0% to 50%) to afford 1-butyl-cyclopropanesulfonic acid amide, as a white solid (0.69 g, 90%): 1H NMR (methanol-d4) □ ppm 0.83 (m, 2H), 0.92 (t, J=7.32 Hz, 2H), 1.24 (m, 2H), 1.34 (m, 2H), 1.47 (m, 2H), 1.87 (m, 2H); 1CNMR (methanol-d4) □ ppm 12.09, 14.25, 23.93, 29.82, 32.38, 41.92.

Workup

customThe solvent was removed in vacuo
customthe residue was chromatographed over SiO2 eluting with EtOAC/Hexanes (0% to 50%)

Sources & evidence

ORD record: ord-c7ad0e93bc5c4f928ca80d151a71e5e0
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878722B2

Reaction notes

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