Acetyl chloride → HCID 69598033, compound

HRID 724685Notes

Reaction equation

HRID 724685 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[S:16](=[O:18])(=[O:17])[N:15]([O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:14](=[O:26])[CH:13]2[CH3:27])=[C:8]([Br:28])[CH:7]=1)(=O)C.C(Cl)(=O)C>C(#N)C.CO>[Br:28][C:8]1[CH:7]=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][C:9]=1[CH:12]1[S:16](=[O:18])(=[O:17])[N:15]([O:19][CH2:20][CH2:21][Si:22]([CH3:24])([CH3:23])[CH3:25])[C:14](=[O:26])[CH:13]1[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 69597691HCID 69597691, compound

Product 1

HCID 69598033HCID 69598033, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-bromo-4-(1,1-dioxido-3-oxo-2-[2-(trimethylsilyl)ethoxy]-methylisothiazolidin-5-yl)benzyl acetate (10 mg, 0.02 mmol) in acetonitrile (0.5 mL) and methanol (0.5 mL) was added acetyl chloride (2.9 μL, 0.041 mmol) at room temperature. The resulting solution was stirred for 24 h and then the reaction was concentrated. The residue was purified by silica gel chromatography (5%–40% ethyl acetate/hexanes) to afford product as oil (8.0 mg, 87%). 1H NMR (400 MHz, CDCl3): δ 7.74 (m, 1H), 7.36 (m, 2H), 5.54 (dd, J=8.0, 6.3 Hz, 1H), 5.07 (dd, J=16.4, 11.3 Hz, 2H), 4.73 (d, J=5.6 Hz, 2H), 3.66 (dd, J=9.4, 7.4 Hz, 2H), 3.50 (dd, J=17.6, 8.0 Hz, 1H), 3.24 (dd, J=17.6, 6.3 Hz, 1H), 1.82 (t, J=5.6 Hz, 1H), 0.96 (dd, J=9.4, 7.4 Hz, 2H), 0.01 (s, 9H). LCMS found for C16H24BrNO5SSiNa (M+Na)+: m/z=472, 474.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe residue was purified by silica gel chromatography (5%–40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c1eabfc1cfcb4d6ab8dc71381d9acc8b
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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