Triethylsilane → Methyl 2-[4-([4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoate

HRID 724701

Reaction equation

HRID 724701 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1)=[O:2].O[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:34](=[O:36])(=[O:35])[NH:33][C:32](=[O:37])[CH:31]=2)=[CH:26][CH:25]=1.C([SiH](CC)CC)C>Cl.O1CCOCC1>[O:35]=[S:34]1(=[O:36])[C:30]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][O:2][CH2:1][C:3]3[CH:21]=[CH:20][C:6]([O:7][C:8]4[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:9]=4[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=3)=[CH:25][CH:26]=2)=[CH:31][C:32](=[O:37])[NH:33]1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 218788375-[4-(Hydroxymethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxideHCID 21879099Methyl 2-(4-formylphenoxy)-6-methoxybenzoate

Product 1

HCID 58746605Methyl 2-[4-([4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)benzyl]oxymethyl)phenoxy]-6-methoxybenzoateYield 6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-(4-formylphenoxy)-6-methoxybenzoate (0.071 g, 0.24 mmol) and 5-[4-(hydroxymethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide (0.050 g, 0.21 mmol) were dissolved in 4 M hydrogen chloride in 1,4-dioxane (2.1 m). The reaction was stirred at ambient temperature for 1.25 h. Triethylsilane (0.13 mL, 0.84 mmol) was added and stirred for 18 h. The reaction was quenched with acetone and evaporated. The product was purified on a 50 mm Luna C18 column using a 20–100% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 30 mL per minute over a 30 minute period. The product was lyophilized to give a white powder (6 mg, 6%). 1H NMR (400 MHz, CDCl3): δ 7.79 (d, J=8.4 Hz, 2H), 7.53 (d, J=8.1 Hz, 2H), 7.32 (m, 2H), 6.71 (s, 1H), 6.69 (d, J=8.5 Hz, 1H), 6.49 (d, J=8.3 Hz, 1H), 4.62 (m, 2H), 4.55 (m, 2H), 3.87 (s, 3H), 3.85 (s, 3H); LCMS found for C26H23NNaO8S (M+Na)+: m/z=532.0.

Workup

  1. stirringstirred for 18 h
  2. customThe reaction was quenched with acetone
  3. customevaporated
  4. customThe product was purified on a 50 mm Luna C18 column
  5. customover a 30 minute

Sources & evidence

ORD record
ord-114ff7770eb54feca447758c34f78314
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Linked notes

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