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

HRID 724701

반응식

HRID 724701 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-114ff7770eb54feca447758c34f78314
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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