Formaldehyde → Chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate

HRID 2357742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2357742
[NH2:1][S:2]([C:5]1[C:6]([Cl:32])=[CH:7][C:8]([NH:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[C:9]([CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20](Cl)=[O:21])=[O:11])(=[O:4])=[O:3].C=[O:34].Cl[CH2:36][Cl:37]>>[NH2:1][S:2]([C:5]1[C:6]([Cl:32])=[CH:7][C:8]([NH:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[C:9]([CH:24]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:23])[CH2:18][CH2:19][C:20]([O:34][CH2:36][Cl:37])=[O:21])=[O:11])(=[O:3])=[O:4]

Komponenten

4

Edukt 3

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 866134344-(3-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride

Produkt 1

HCID 68457545Chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoyl chloride (813) (0.040 mole) and paraformaldehyde (0.040 mole) is heated in a sealed vessel at 90° C. for 3 hours. The reaction is cooled, and the solids are dissolved in dichloromethane. The solution is washed with 5% aqueous sodium bicarbonate, with water, and then with a saturated sodium chloride solution. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo to give crude product, which may be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent. The fractions that contain pure product may be combined and spin evaporated in vacuo to give chloromethyl 4-(3-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)propoxy)(4-oxo)butanoate (815). See eg., Bodor, et al., J. Med. Chem., 23, 469 (1980), and Ulich, et al., J. Am. Chem. Soc., (1921) 43: 660.

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. washThe solution is washed with 5% aqueous sodium bicarbonate, with water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give crude product, which
  7. custommay be purified by column chromatography on silica gel with hexanes/ethyl acetate as eluent
  8. customspin evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f4d17efbb9f24fee8dede1ab8574be29
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07763612B2

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