Phenylacetylene → tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]morpholine-4-carboxylate

HRID 629721

Reaktionsgleichung

Reaktionsgleichung von HRID 629721
[N:1]([CH2:4][C@H:5]1[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][C@@H:8]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:27](=[O:47])[C@H:28]([CH:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[NH:29][C:30]([O:32][CH3:33])=[O:31])[O:7][CH2:6]1)=[N+:2]=[N-:3].[C:48]1([C:54]#[CH:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.CCN(C(C)C)C(C)C>O1CCCC1.[Cu]I>[CH3:33][O:32][C:30]([NH:29][C@H:28]([C:27]([NH:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][CH2:18][C@H:8]1[O:7][CH2:6][C@@H:5]([CH2:4][N:1]2[CH:55]=[C:54]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:3]=[N:2]2)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:9]1)=[O:47])[CH:34]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:31]

Komponenten

6

Edukt 3

HCID 10821PhenylacetyleneHCID 81531DiisopropylethylamineHCID 86726323tert-butyl (2R,5R)-5-(azidomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate

Produkt 1

HCID 86726324tert-butyl (2R,5R)-2-[2-(2-{[N-(methoxycarbonyl)-beta-phenyl-L-phenylalanyl]amino}phenyl)ethyl]-5-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of tert-butyl (2R,5R)-5-(azidomethyl)-2-[2-(2-{[N-(methoxycarbonyl)-β-phenyl-L-phenylalanyl]amino}phenyl)ethyl]morpholine-4-carboxylate (1 eq.) in tetrahydrofuran (0.033M) were added phenylacetylene (3.9 eq.) and Hunig's base (5 eq.). Nitrogen was then bubbled for 5 minutes through the reaction mixture which was placed in a sealed tube. Copper(I) iodide (1.5 eq.) was added to the reaction mixture and the temperature was raised to 70° C. for 16 hrs. The reaction mixture was evaporated to dryness and the evaporation residue was purified by automated silica gel flash chromatography system eluted with a gradient 0% to 10% of MeOH/CH2Cl2.

Aufarbeitung

  1. customNitrogen was then bubbled for 5 minutes through the reaction mixture which
  2. customwas placed in a sealed tube
  3. customThe reaction mixture was evaporated to dryness
  4. customthe evaporation residue was purified by automated silica gel flash chromatography system
  5. washeluted with a gradient 0% to 10% of MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-cc0a8d29250a403d9020ce494a36b21e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315475B2

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