Trifluoroacetic acid → HCID 21878746, compound

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14](=[O:16])(=[O:15])[N:13](C(C)(C)C)[C:12](=[O:21])[CH:11]=2)=[CH:6][CH:5]=1.C([SiH](C(C)C)C(C)C)(C)C.[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14](=[O:16])(=[O:15])[NH:13][C:12](=[O:21])[CH:11]=2)=[CH:6][CH:5]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 138754Silane, tris(1-methylethyl)-

HCID 218793845-[4-(2-Amino-ethyl)-phenyl]-2-tert-butyl-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

Product 1

HCID 21878746HCID 21878746, compoundYield 60%

Procedure

23-E (262 mg, 0.850 mmol) was dissolved in trifluoroacetic acid (10 mL) and triisopropylsilane (1 mL) was added. The reaction was heated to reflux under an atmosphere of nitrogen overnight. The reaction was cooled to room temperature then concentrated via rotovap. The reaction material was chromatographed on a 50 mm Luna C18 column using a 0–30% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 30 mL per minute over a 20 minute period. The major fraction was lyophilized to give a white powder (0.128 g, 60%). 1H NMR (500 MHz, CD3OD): δ 7.89 (d, J=9.0 Hz, 2H), 7.51 (d, J=9.0 Hz, 2H), 7.06 (s, 1H), 3.25 (t, J=7.2 Hz, 2H), 3.06 (t, J=7.2 Hz, 2H); LCMS found for C11H13N2O3S (M+H)+: m/z=253.