Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylate → 2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester

HRID 29765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29765
[C:1]1([CH2:7][CH2:8][CH2:9][PH:10](=[O:12])[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([O:15][C:16](=[O:34])[C:17]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)=[CH2:18])[CH3:14]>CC#N>[CH2:13]([O:15][C:16](=[O:34])[CH:17]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])=[CH:24][CH:25]=1)[CH2:18][P:10]([OH:11])([CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12])[CH3:14]

Komponenten

4

Edukt 2

HCID 54494317Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylateHCID 178527054HCID 178527054, Verbindung

Produkt 1

HCID 541967722-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl esterAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (3-Phenyl-propyl)-phosphinic acid (0.579 g 3.143 mmol) and 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.327 g 1.067 mmol) in MeCN (7.5 mL) was degassed using the freeze-thaw technique. BSA (2.55 g 12.57 mmol) was added and the mixture was stirred for 3 days and concentrated under reduced pressure. The residue was dissolved in chloroform, washed with NaHCO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (CH2Cl2/MeOH, 8:2) gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester (0.240 g, 16%).

Aufarbeitung

  1. additionBSA (2.55 g 12.57 mmol) was added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with NaHCO3 and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-01691e857ae147da98817726457188e2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423012B2

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