tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate → (2S)-2-{2-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyric acid

HRID 1251927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251927
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH2:7][C:8]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([C:38]3[S:39][CH:40]=[CH:41][N:42]=3)[CH2:31][C:32]3[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=3)=[CH:25][C:9]=2[C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][S:23][CH3:24])[C:14]([O:16]C(C)(C)C)=[O:15])=[O:11])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH2:7][C:8]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([C:38]3[S:39][CH:40]=[CH:41][N:42]=3)[CH2:31][C:32]3[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=3)=[CH:25][C:9]=2[C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][S:23][CH3:24])[C:14]([OH:16])=[O:15])=[O:11])=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 57100633tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate

Produkt 1

HCID 57278593(2S)-2-{2-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyric acidAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate (0.050 g, 0.078 mmol) in TFA was stirred at ambient temperature under a nitrogen atmosphere for 4 hours. The TFA was evaporated away and the residues basified with saturated sodium bicarbonate solution, reacidified with 2NHCl to pH6 and extracted with dichloromethane. The extracts were dried and evaporated to dryness. The residue was dried under high vacuum to give the title compound as a white solid (0.040 g, 89%).

Aufarbeitung

  1. customThe TFA was evaporated away
  2. extractionextracted with dichloromethane
  3. customThe extracts were dried
  4. customevaporated to dryness
  5. customThe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c58db41caf9e41aba7dfba50f2137d4f
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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