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1,2-Dichloroethane → 4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide

HRID 1859287
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1859287
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:30]=[CH:29][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH:20]4[CH:25]([C:26]([OH:28])=O)[NH:24][CH2:23][CH2:22][S:21]4)(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:8][CH:7]=2)=[CH:2]1.[Si](O[NH2:49])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(Cl)CCl>ClCCl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:30]=[CH:29][C:9]([O:10][C:11]3[CH:12]=[CH:13][C:14]([S:17]([CH:20]4[CH:25]([C:26]([NH2:49])=[O:28])[NH:24][CH2:23][CH2:22][S:21]4)(=[O:18])=[O:19])=[CH:15][CH:16]=3)=[CH:8][CH:7]=2)=[CH:2]1
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Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 11737343O-(tert-Butyldiphenylsilyl)hydroxylamineHCID 865886704-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid

Produkt 1

HCID 865886724-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamideAusbeute 14,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 3(S)-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid (293 mg, 0.62 mmol) and O-(tert-butyldiphenylsilyl)hydroxylamine (0.22 g, 0.8 mmol) in 5 mL of dichloromethane was added EDC (132 mg, 0.69 mmol). After 18 hours at 25° C., the mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane. The aqueous layer was extracted twice with dichloromethane, and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel, eluting with a gradient from dichloromethane to 5% methanol in dichloromethane, to provide 3(S)-N-(tert-butyldiphenylsilyl)oxy-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxamide (40 mg, 8%). FAB+MS Calcd for M+Cs+ =859.1308 Obs 859.1274; 1HNMR (d6 -DMSO): δ10.81 (s, 1H), 8.17 (s, 1H), 7.74 (s, 1H), 7.67-7.61 (m, 8H), 7.45-7.30 (m, 6H), 7.10 (d, 2H, J=8.83 Hz), 7.00 (d, 2H, J=8.46 Hz), 6.94 (s, 1H), 4.06 (s, 1H), 3.95-3.89 (bm, 1H), 3.77-3.73 (bm, 1H), 2.87-2.78 (bm, 1H), 1.28 (s, 3H), 0.99 (s, 9H), 0.61 (s, 3H)

Aufarbeitung

  1. customthe mixture was partitioned between 1 N aq. sodium bisulfate and dichloromethane
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with a gradient from dichloromethane to 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-76bd95b4c8c743baaba41354f040773f
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06153757

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