Triphenylphosphine → methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate

HRID 465622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465622
O[CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].[C:22]([O:26][NH:27][S:28]([CH:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]1=[C:38]=[O:39])(=[O:30])=[O:29])([CH3:25])([CH3:24])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:22]([O:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[S:28]([CH:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]1=[C:38]=[O:39])(=[O:30])=[O:29])([CH3:25])([CH3:23])[CH3:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10017284methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoateHCID 86746178HCID 86746178, Verbindung

Produkt 1

HCID 86746177methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate (1.09 g 3.7 mmol), N-t-butoxy-carbonyl-p-chlorophenylsulfonamide (1.52 g, 5.2 mmol) and triphenylphosphine (1.92 g, 7.3 mmol) in methylene chloride (17 ml) is added dropwise diethyl azodicarboxylate (0.82 ml, 5.2 mmol). The reaction mixture is allowed to stir or 1 hour and the solvent is evaporated. The residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane to obtain methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate; IR (CH2Cl2): 1730, 1356, 1154 cm- 1.

Aufarbeitung

  1. customthe solvent is evaporated
  2. customThe residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c01535285c094031aee9ef8e5fdd525f
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153214

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