5-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-2-tert-butyl-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one → 5-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724605Notes

Reaction equation

HRID 724605 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[S:28](=[O:30])(=[O:29])[N:27](C(C)(C)C)[C:26](=[O:35])[CH:25]=1>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:4][C:3]=1[C:24]1[S:28](=[O:29])(=[O:30])[NH:27][C:26](=[O:35])[CH:25]=1

Participants

3

Reactant 1

HCID 587465655-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-2-tert-butyl-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

Product 1

HCID 587465375-[2-Bromo-4-(3-oxo-2,3-diphenyl-propyl)-phenyl]-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.36-B (12 mg, 22 μmol) in trifluoroacetic acid (2.5 mL) was heated at 150° C. in a microwave for 30 sec. The reaction mixture was concentrated to a crude residue which was purified by preparative LCMS to yield the desired product (7 mg, 65%). 1H NMR (400 MHz, CDCl3): δ 7.91 (d, J=7.2 Hz, 2H), 7.75 (d, J=8.0 Hz, 1H), 7.52–7.47 (m, 2H), 7.37 (dd, J=7.8, 7.6 Hz, 2H), 7.32–7.21 (m, 6H), 7.00 (s, 1H), 4.79 (dd, J=7.4, 7.2 Hz, 1H), 3.57 (dd, J=13.7, 7.6 Hz, 1H), 3.10 (dd, J=13.9, 6.8 Hz, 1H); LCMS found for C24H19BrNO4S (M+H)+: m/z=496.

Workup

  1. concentrationThe reaction mixture was concentrated to a crude residue which
  2. customwas purified by preparative LCMS

Sources & evidence

ORD record
ord-9b77ecf23d2d447e9bfe73acc1b14a25
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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