5-Hexenoic Acid → N-((2S,3R)-4-((1R,3R)-3-(allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl)hex-5-enamide

HRID 501762

Reaktionsgleichung

Reaktionsgleichung von HRID 501762
[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@@H:7]([NH:15][CH2:16][C@@H:17]([OH:29])[C@@H:18]([NH2:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:6]1)[CH:2]=[CH2:3].[C:30](O)(=[O:36])[CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35]>CC(=O)OCC>[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C@H:7]([NH:15][CH2:16][C@@H:17]([OH:29])[C@@H:18]([NH:28][C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH:34]=[CH2:35])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:6]1)[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 153085-Hexenoic AcidHCID 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 68460708N-((2S,3R)-4-((1R,3R)-3-(allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl)hex-5-enamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Step EE (1): (2R,3S)-1-((1S,3R)-3-(Allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-3-amino-4-(3,5-difluorophenyl)butan-2-ol from Step EA (1) was coupled with hex-5-enoic acid by following a procedure analogous to Step EA (2) to afford 1.9 g (62% yield) of N-((2S,3R)-4-((1R,3R)-3-(allyloxy)-6-bromo-2,3-dihydro-1H-inden-1-ylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl)hex-5-enamide. MS (M+2H)+ 564.95. 1H NMR (500 MHz, CDCl3) δ ppm 1.58-1.69 (m, 3H) 1.87-2.00 (m, 4H) 2.03-2.16 (m, 2H) 2.64-2.73 (m, 2H) 2.76-2.85 (m, 2H) 3.04 (dd, J=14.34, 4.58 Hz, 1H) 3.48-3.53 (m, 1H) 4.04-4.21 (m, 4H) 4.76 (t, J=5.80 Hz, 1H) 4.93 (s, 1H) 4.96 (dd, J=3.51, 1.37 Hz, 1H) 5.20 (dd, J=10.38, 1.22 Hz, 1H) 5.28-5.34 (m, 1H) 5.60-5.76 (m, 2H) 5.90-5.99 (m, 1H) 6.63-6.68 (m, 1H) 6.73-6.78 (m, 2H) 7.28 (d, J=8.24 Hz, 1H) 7.41 (dd, J=7.93, 1.83 Hz, 1H) 7.51 (s, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-e4b8ed104c6f4fc19b1f5615b1f36da3
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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