Trifluoroacetic acid → 5-[4-(2-aminoethyl)phenyl]-2-tert-butylisothiazol-3(2H)-one 1,1-dioxide Trifluoroacetate

HRID 724694Notes

Reaction equation

HRID 724694 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20](=[O:22])(=[O:21])[N:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:18](=[O:27])[CH:17]=2)=[CH:12][CH:11]=1)(C)(C)C.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>C(Cl)Cl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[NH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20](=[O:22])(=[O:21])[N:19]([C:23]([CH3:25])([CH3:24])[CH3:26])[C:18](=[O:27])[CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 587468002-[4-(2-tert-Butyl-1,1,3-trioxo-2,3-dihydro-1H-1lambda6-isothiazol-5-yl)-phenyl]-ethyl-carbamic acid tert-butyl ester

Product 1

HCID 218793835-[4-(2-aminoethyl)phenyl]-2-tert-butylisothiazol-3(2H)-one 1,1-dioxide TrifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[4-(2-tert-Butyl-1,1,3-trioxo-2,3-dihydro-1H-1λ6-isothiazol-5-yl)-phenyl]-ethyl-carbamic acid tert-butyl ester (200 mg, 0.490 mmol) was dissolved in methylene chloride (2 mL) and trifluoroacetic acid (2 mL) and the reaction was stirred for 2 h. The reaction was chromatographed on a 21 mm Luna C18 column using a 10–90% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 12.5 mL per minute over a 15 minute period. The major fraction was lyophilized to give a white powder (207 mg, 100%). 1H NMR (500 MHz, CDCl3): δ 7.90 (m, 2H), 7.52 (m, 2H), 3.25 (t, J=6.5 Hz, 2H), 3.06 (t, J=7.4 Hz, 2H), 1.73 (s, 9H); LCMS found for C17H22F3N2O5S (M+H)+: m/z=309.2.

Workup

  1. customThe reaction was chromatographed on a 21 mm Luna C18 column
  2. customover a 15 minute

Sources & evidence

ORD record
ord-3bf130b0c1184fc7836f5941c142410d
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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