Methyl morpholine oxide → (2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

HRID 563837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563837
[CH2:1]([NH:8][C:9](=[O:36])[N:10]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[C:26]([CH2:32][C:33]([OH:35])=[O:34])[CH:25]=1)[CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37]([O:44][C:45]([C@@H:47]1[C@@H:52]([OH:53])[C@H:51]([OH:54])[C@@H:50]([OH:55])[C@H:49](O)[O:48]1)=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N+]1([O-])CCOCC1>CC#N>[CH2:37]([O:44][C:45]([C@@H:47]1[C@@H:52]([OH:53])[C@H:51]([OH:54])[C@@H:50]([OH:55])[C@H:49]([O:34][C:33](=[O:35])[CH2:32][C:26]2[CH:25]=[C:24]([C:15]3[CH:16]=[CH:17][C:18]([C:20]([F:22])([F:23])[F:21])=[CH:19][C:14]=3[CH2:13][N:10]([CH2:11][CH3:12])[C:9]([NH:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:36])[C:29]([O:30][CH3:31])=[CH:28][CH:27]=2)[O:48]1)=[O:46])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Komponenten

6

Edukt 4

HCID 82029Methyl morpholine oxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44158492Am-211HCID 58148857(2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate

Produkt 1

HCID 66607701(2S,3S,4S,5R,6S)-6-{2-[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

[2′-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid (0.110 g, 0.2 mmol), (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester (0.060 g, 0.2 mmol), HATU (0.026 g, 0.2 mmol), and N-methylmorpholine-N-oxide (0.05 mL, 0.4 mmol) were combined in MeCN (2 mL) and stirred for 2 days at room temperature. The mixture was concentrated, and the residue was purified by preparative HPLC to give the title compound.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3b59b7eadfad4c0fb3f27b75652f6e6e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067445B2

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