Ethanol → 4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid

HRID 23173

Reaktionsgleichung

Reaktionsgleichung von HRID 23173
Br[C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH:16]3[CH:21]([C:22]([OH:24])=[O:23])[NH:20][CH2:19][CH2:18][S:17]3)(=[O:15])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[O:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]1.C(O)C>C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:27]1[CH:31]=[CH:30][C:29]([C:2]2[CH:26]=[CH:25][C:5]([O:6][C:7]3[CH:8]=[CH:9][C:10]([S:13]([CH:16]4[CH:21]([C:22]([OH:24])=[O:23])[NH:20][CH2:19][CH2:18][S:17]4)(=[O:15])=[O:14])=[CH:11][CH:12]=3)=[CH:4][CH:3]=2)=[CH:28]1

Komponenten

7

Edukt 3

HCID 702EthanolHCID 2734358Furan-3-boronic acidHCID 865886714-(4-bromophenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid

Produkt 1

HCID 865886704-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acidAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 0.45 g (1.0 mmol) of 3(S)-4-(4-(4-bromophenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid and 0.11 g (1.0 mmol) of 3-furan boronic acid (J. Org. Chem. 1984, 49, 5237-5243) in 2 mL of benzene, 2 mL of 2M aq. sodium carbonate, and 1.5 mL of ethanol was deoxygenated with a stream of argon for 15 minutes, and then 115 mg (0.1 mmol) of tetrakis(triphenylphosphine)palladium was added and the mixture was heated at 80° C. for six days. After cooling to room temperature, the mixture was partitioned between ethyl acetate and pH 4 citrate buffer. The aqueous layer was extracted twice with ethyl acetate, 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)-4-(4-(4-(furan-3-yl)phenoxy)benzenesulfonyl-tetrahydro-2H-1,4-thiazine-3-carboxylic acid (0.317 g, 67%) as a sticky solid foam. FAB+MS Calcd for M+Cs+=606.0021. Obs 606.0036; 1H NMR (CDCl3) δ 7.72-7.43 (m, 6H), 7.04 (d, 2H, J=8.46 Hz), 7.00 (d, 2H, J=8.82 Hz), 6.67 (s, 1H), 4.51 (s, 1H), 4.1-3.9 (bm, 1H), 3.7-3.6 (bm, 1H), 3.2-3.1 (bm, 1H), 2.42 (bd, 1H, J=12.87 Hz), 1.61 (s, 3H), 1.38 (s, 3H)

Aufarbeitung

  1. customwas deoxygenated with a stream of argon for 15 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was partitioned between ethyl acetate and pH 4 citrate buffer
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with a gradient from dichloromethane to 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4680cbedb8364560ab87f775821d48ad
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849732B2

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