Phthalaldehyde → 2-(2R)-(4-Chlorobiphenylsulfonylamino)-5-(1-oxo-1,3-dihydro-isoindol-2-yl) pentanoic acid

HRID 277171

Reaktionsgleichung

Reaktionsgleichung von HRID 277171
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([S:15]([NH:18][C@H:19]([CH2:23][CH2:24][CH2:25][NH2:26])[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.[CH:27](=O)[C:28]1[C:29](=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH:30]=[O:31]>C(O)(=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([S:15]([NH:18][C@H:19]([CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][C:28]3[C:29](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:31])[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 4807PhthalaldehydeHCID 700635182-(2R)-(4-chlorobiphenylsulfonylamino)-5-amino-pentanoic acid hydrochloride

Produkt 1

HCID 186827332-(2R)-(4-Chlorobiphenylsulfonylamino)-5-(1-oxo-1,3-dihydro-isoindol-2-yl) pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

0.32 g (0.76 mmol) of 2-(2R)-(4-chlorobiphenylsulfonylamino)-5-amino-pentanoic acid hydrochloride is dissolved in 30 ml of glacial acetic acid with 0.186 g (1.35 mmol) of phthalaldehyde and stirred at 100° C. for 3 hours. The solution is cooled to 0° C., and the precipitate which is deposited is filtered off with suction and chromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2).

Aufarbeitung

  1. temperatureThe solution is cooled to 0° C.
  2. filtrationthe precipitate which is deposited is filtered off with suction
  3. customchromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2)

Quellen und Nachweise

ORD-Eintrag
ord-5c33ebce0a094670b3bde37bb97a650e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355673B1

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