Triphenylphosphine → 1,1-Dimethylethyl N-[(1R)-2-[5-bromo-3-[(2,6-difluorophenyl)methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]carbamate

HRID 574244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574244
[Br:1][C:2]1[C:3](=[O:19])[NH:4][C:5](=[O:18])[N:6]([CH2:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])[C:7]=1[CH3:8].[C:20]([O:24][C:25](=[O:36])[NH:26][C@H:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:28]O)([CH3:23])([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:20]([O:24][C:25](=[O:36])[NH:26][C@H:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:28][N:4]1[C:3](=[O:19])[C:2]([Br:1])=[C:7]([CH3:8])[N:6]([CH2:9][C:10]2[C:11]([F:17])=[CH:12][CH:13]=[CH:14][C:15]=2[F:16])[C:5]1=[O:18])([CH3:21])([CH3:22])[CH3:23]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl esterHCID 120945185-Bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione

Produkt 1

HCID 114328141,1-Dimethylethyl N-[(1R)-2-[5-bromo-3-[(2,6-difluorophenyl)methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]carbamateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione (synthesized according to the method of BMCL 2004 14(19) 4967-4973) (2.77 g, 8.37 mmol), ((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (2.08 g, 8.78 mmol), and triphenylphosphine (3.29 g, 12.5 mmol) were added to anhydrous tetrahydrofuran (70 mL) and stirred for a short time. To this solution was slowly added diethylazodicarboxylate (1.95 mL, 12.5 mmol), followed by stirring at room temperature for 12 hrs in a nitrogen atmosphere. Following concentration, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate, 2/1) and dried in a vacuum to afford 2.26 g of the compound as a white foam (yield 49%).

Aufarbeitung

  1. stirringby stirring at room temperature for 12 hrs in a nitrogen atmosphere
  2. concentrationconcentration
  3. customthe residue was purified
  4. customdried in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-13896cc8b92445f9b29c8a33216235e8
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034850B2

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