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Phosphorus pentachloride → Methyl 4-[1-(aminosulfonyl)-3-methoxy-3-oxopropyl]-3-bromobenzoate

HRID 724677
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 724677
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:12]([S:18]([OH:21])(=O)=[O:19])[CH2:13][C:14]([O:16][CH3:17])=[O:15].[N:22]1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[OH-].N>C(Cl)Cl>[NH2:22][S:18]([CH:12]([C:3]1[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]=1[Br:1])[CH2:13][C:14]([O:16][CH3:17])=[O:15])(=[O:21])=[O:19]
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Komponenten

5

Edukt 3

HCID 24819Phosphorus pentachlorideHCID 21862953Ammonia hydroxideHCID 866020801-[2-bromo-4-(methoxycarbonyl)phenyl]-3-methoxy-3-oxopropane-1-sulfonic Acid pyridine

Produkt 1

HCID 21878646Methyl 4-[1-(aminosulfonyl)-3-methoxy-3-oxopropyl]-3-bromobenzoateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

1-[2-bromo-4-(methoxycarbonyl)phenyl]-3-methoxy-3-oxopropane-1-sulfonic acid—pyridine (1:1) (0.220 g, 0.478 mmol) was dissolved in methylene chloride (2 mL) at room temperature, and phosphorus pentachloride (0.199 g, 0.956 mmol) were added. The mixture was stirred overnight. The reaction solution was cannulated into a 2 mL ammonia hydroxide solution at 0° C. dropwise. After stirring for 1 h, the organic layer was isolated, aqueous layer was extracted with methylene chloride twice. The combined organic solutions were dried over sodium sulfate, filtered, concentrated. The residue was purified by preparative LCMS to afford product as slight yellow solid (114 mg, 63%). 1H NMR (400 MHz, CD3OD): δ 8.24 (d, J=1.5 Hz, 1H), 7.99 (dd, J=8.2, 1.5 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 5.39 (dd, J=10.1, 4.9 Hz, 1H), 3.91 (s, 3H), 3.58 (s, 3H), 3.43 (dd, J=16.6, 4.9 Hz, 1H), 3.18 (dd, J=16.6, 10.1 Hz, 1H). LCMS found for C12H14BrNO6SNa (M+Na)+: m/z=401, 403.

Aufarbeitung

  1. stirringAfter stirring for 1 h
  2. customthe organic layer was isolated
  3. extractionaqueous layer was extracted with methylene chloride twice
  4. dry with materialThe combined organic solutions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-4fa5b2e886ab488e8683667fdb4f23ee
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07141596B2

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