Water → HCID 131727519, Verbindung

HRID 1988286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988286
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.[NH:22]([CH3:47])[C@H:23]([C:27]([N:29]([CH3:46])[C@H:30]([C:43]([NH2:45])=[O:44])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH:33]=1)=[O:28])[CH:24]([CH3:26])[CH3:25].O>C1COCC1>[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([N:22]([CH3:47])[C@H:23]([C:27]([N:29]([CH3:46])[C@H:30]([C:43]([NH2:45])=[O:44])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C:39]([CH3:42])([CH3:40])[CH3:41])[CH:33]=1)=[O:28])[CH:24]([CH3:26])[CH3:25])=[O:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 21970629N-(tert-Butoxycarbonyl)-3-fluoro-L-tyrosineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Produkt 1

HCID 131727519HCID 131727519, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the above crude Boc-Tyr(3-F)-OH (1.18 g), N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.10 g, 3.03 mmol) and CMPI (1.16 g, 4.55 mmol) in THF (6 ml), TEA (1.27 ml, 12.1 mmol) was added under cooling with ice and stirred at room temperature for 27 hours. The reaction mixture was mixed with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: chloroform:methanol:concentrated aqueous ammonia=30:1:0.05), giving the titled compound (0.19 g, 10%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80ee00a960f64f3db7aa44c56d617f7a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553969B1

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