5-Hexenoic Acid → N-((2R,3S)-1-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(tert-butyldimethylsilyloxy)-5-methylhexan-3-yl)hex-5-enamide

HRID 501763

Reaktionsgleichung

Reaktionsgleichung von HRID 501763
C(O[C@H]1C2C(=CC(Br)=CC=2)[C@@H](NC[C@@H](O)[C@@H](N)CC2C=C(F)C=C(F)C=2)C1)C=C.[C:30]([OH:37])(=O)[CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35].[CH2:38]([O:41][C@H:42]1[C:50]2[C:45](=[CH:46][C:47]([O:51][CH:52]([CH3:54])[CH3:53])=[CH:48][CH:49]=2)[C@@H:44]([NH:55][CH2:56][C@@H:57]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:67])[CH3:66])[C@@H:58]([NH2:63])[CH2:59][CH:60]([CH3:62])[CH3:61])[CH2:43]1)[CH:39]=[CH2:40]>>[CH2:38]([O:41][C@H:42]1[C:50]2[C:45](=[CH:46][C:47]([O:51][CH:52]([CH3:54])[CH3:53])=[CH:48][CH:49]=2)[C@@H:44]([NH:55][CH2:56][C@@H:57]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:66])[CH3:67])[C@@H:58]([NH:63][C:30](=[O:37])[CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35])[CH2:59][CH:60]([CH3:61])[CH3:62])[CH2:43]1)[CH:39]=[CH2:40]

Komponenten

4

Edukt 3

HCID 153085-Hexenoic AcidHCID 59423736(2R,3S)-N1-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-yl)-2-(tert-butyldimethylsilyloxy)-5-methylhexane-1,3-diamineHCID 68465135(2R,3S)-1-((1S,3R)-3-(Allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol2×

Produkt 1

HCID 68463755N-((2R,3S)-1-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(tert-butyldimethylsilyloxy)-5-methylhexan-3-yl)hex-5-enamide

Versuchsvorschrift

Step EQ (1): Hex-5-enoic acid (240 mg, 2.1 mmol) and (2R,3S)-N1-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-yl)-2-(tert-butyldimethylsilyloxy)-5-methylhexane-1,3-diamine (1.1 g, 2.2 mmol, from Preparation BH) were coupled using a procedure analogous to Step CA (1) to afford N-((2R,3S)-1-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-ylamino)-2-(tert-butyldimethylsilyloxy)-5-methylhexan-3-yl)hex-5-enamide. LC-MS (M+H)+=587.47.

Quellen und Nachweise

ORD-Eintrag
ord-d00ebbce7b2f4427a377d14caf225669
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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