Lithium Hydroxide → 2-[(1-Benzyloxycarbonylamino-2-methyl-propyl)-hydroxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid

HRID 29744

Reaktionsgleichung

[Li+].[OH-].C[O:4][C:5](=[O:38])[CH:6]([O:18][P:19]([CH:23]([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[CH:24]([CH3:26])[CH3:25])([O:21]C)=[O:20])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(#N)C>[CH2:31]([O:30][C:28]([NH:27][CH:23]([P:19]([OH:21])([O:18][CH:6]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[C:5]([OH:38])=[O:4])=[O:20])[CH:24]([CH3:25])[CH3:26])=[O:29])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

1 M LiOH (5 mL) was added to a solution of 2-[(1-benzyloxycarbonylamino-2-methylpropyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (187 mg, 0.35 mmol) in acetonitrile (5 mL). The mixture was stirred at 50° C. over night and concentrated under reduced pressure. The crude product was purified using chromathography (iPrOH/conc. aq. NH3/H2O, 4:2:1) to yield 2-[(1-benzyloxycarbonylamino-2-methyl-propyl)-hydroxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid (180 mg, 100%).

Aufarbeitung

concentrationconcentrated under reduced pressure
customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag: ord-b1dee656e0d746948a97118af01a44d1
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423012B2

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