p-Toluenesulfonic acid → 2-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

HRID 744829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 744829
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N[C:17](=[O:52])[C@H:18]([CH3:51])[CH2:19][C@H:20]([OH:50])[C@@H:21]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:22][C@@H:23]([CH:39]([CH3:41])[CH3:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)CCC>C(Cl)(Cl)Cl>[C:46]([O:45][C:43]([NH:42][C@H:21]([CH:20]1[CH2:19][C@@H:18]([CH3:51])[C:17](=[O:52])[O:50]1)[CH2:22][C@@H:23]([CH:39]([CH3:40])[CH3:41])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)=[O:44])([CH3:49])([CH3:48])[CH3:47]

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 236251841,1-Dimethylethyl N-((1S,2S,4R)-5-(butylamino)-2-hydroxy-1-((2S)-2-((4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutyl)-4-methyl-5-oxopentyl)carbamate

Produkt 1

HCID 228657322-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2.02 g of p-toluenesulfonic acid (monohydrate) are added to 5.6 g of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-octanoic acid (N-butyl)-amide (Example 32) in 240 ml of chloroform at room temperature and the mixture is stirred at room temperature for a further 18 hours. The reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and 0.1N hydrochloric acid. The organic phases are concentrated by evaporation and the title compound is obtained from the residue after FC (160 g of silica gel, eluant: ethyl acetate/hexane 1:1): Rf (ethyl acetate/hexane=2:1)=0.47; m.p. 86°-87° C.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and 0.1N hydrochloric acid
  3. concentrationThe organic phases are concentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-7279caf1803e45b5911fad61f0e67347
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559111

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