7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid methyl ester → 7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid

HRID 352406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352406
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][N:10]1[CH:15](/[CH:16]=[CH:17]/[C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12][C:11]1=[O:25]>C(#N)C.P([O-])([O-])([O-])=O>[O:25]=[C:11]1[CH2:12][CH2:13][CH2:14][CH:15](/[CH:16]=[CH:17]/[C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[N:10]1[CH2:9][C:8]#[C:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2]

Komponenten

4

Edukt 1

HCID 104063027-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid methyl ester

Produkt 1

HCID 103156857-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1061PhosphateLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Rabbit liver esterase (134 units/mg, 3 mg) was added to a solution of 7-[2-oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid methyl ester (18 mg, 0.45 mmol) in acetonitrile (0.3 mL) and pH 7.2 phosphate buffer (3.0 mL). After 18.5 h, acetonitrile (10 mL) was added and the reaction mixture was concentrated to dryness in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 17 mg (97%) of the title compound.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo
  2. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-a438957f2d6849ff982db3e9034a98ff
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747037B1

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