Diphenylphosphinic acid → Diphenylphosphoryloxymethyl ketone

HRID 225953

Reaktionsgleichung

Reaktionsgleichung von HRID 225953
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[C:7]1([P:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])[OH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[F-].[K+].CN(C=O)C>[C:7]1([P:13]([O:14][CH2:2][C:3]([CH2:5][O:15][P:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:14])=[O:4])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 15567Diphenylphosphinic acidHCID 699521,3-Dibromo-2-propanone

Produkt 1

HCID 54568997Diphenylphosphoryloxymethyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86608353KF DmfLösungsmittel

Versuchsvorschrift

(2S)-4-(tert-butoxy)-2-({[(5R)-5-isopropyl-3-(1-isoquinolinyl)-4,5-dihydro-5-isoxazolyl]carbonyl}amino)-4-oxobutanoic acid [obtained by coupling reaction of Compound (VIIf) with Asp(O-t-Bu)-OMe and hydrolysis] was reacted according to the same procedure as Preparation 5 to give bromomethyl ketone derivative (tert-butyl (3S)-5-bromo-3-({[(5R)-5-isopropyl-3-(1-isoquinolinyl)-4,5-dihydro-5-isoxazolyl]carbonyl}amino)-4-oxopentanoate). This bromomethyl ketone derivative was reacted with diphenylphosphinic acid in KF/DMF (see Preparation 5) to give diphenylphosphoryloxymethyl ketone derivative, which was then reacted according to the same procedure as Example 2 to give the title compound (Compound of Example 60).

Quellen und Nachweise

ORD-Eintrag
ord-e8bf8f587d1544ea9954eb65e2e1a832
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557133B2

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