Boc-L-Valine → HCID 178448372, Verbindung

HRID 1987708

Reaktionsgleichung

Reaktionsgleichung von HRID 1987708
[CH3:1][CH:2]([C@H:4]([NH2:23])C([O:7][CH2:8][CH2:9][O:10][CH2:11][N:12]1[C:16]2[NH:17][C:18]([NH2:22])=[N:19][C:20](=[O:21])[C:15]=2[N:14]=[CH:13]1)=O)[CH3:3].[NH:24]([C:32]([O:34]C(C)(C)C)=O)[C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27]>C(N(CC)CC)C>[CH:13]1[N:12]([CH2:11][O:10][CH2:9][CH2:8][OH:7])[C:16]2[N:17]=[C:18]([NH2:22])[N:19]=[C:20]([OH:21])[C:15]=2[N:14]=1.[CH3:1][CH:2]([C@H:4]([NH2:23])[C:32]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:27])[CH3:28])=[O:34])[CH3:3]

Komponenten

4

Edukt 2

HCID 83693Boc-L-ValineHCID 178448382HCID 178448382, Verbindung

Produkt 1

HCID 178448372HCID 178448372, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of Boc-Val and dicyclohexyl carbodiimide (DCC) in dimethylformamide (DMF) in a ratio of 1:2 DCC/Boc-Val was stirred for 1 hr at 0° C. under nitrogen atmosphere. A solution of acyclovir (1) and 4-N,N (dimethylamino)pyridine (DMAP) was added to the reaction mixture, stirred for 18 hrs and then filtered. The solvent of the filtrate was partially removed in vacuo and the impure solution was added dropwise to cold diethyl ether. The resulting precipitate (2) was filtered and dried, followed by acidolytic removal (treating Boc-Val-ACV with trifluoroacetic acid (TFA) for 30 min at 0° C.) of the Boc protecting group to yield Val-ACV (3). Compound (3) was neutralized by triethylamine (TEA) and treated with the amino acid anhydride of Boc-Val for about 5 hrs. The solvent was removed from the reaction mixture in vacuo and the reaction mixture was added dropwise to the cold diethyl ether. The resulting precipitate (4) was filtered, dried and the Boc group was deprotected (acidolytic removal) to yield the desired dipeptide ester of acyclovir Val-Val-ACV (5).

Aufarbeitung

  1. customThe solvent was removed from the reaction mixture in vacuo
  2. additionthe reaction mixture was added dropwise to the cold diethyl ether
  3. filtrationThe resulting precipitate (4) was filtered
  4. customdried
  5. custom(acidolytic removal)

Quellen und Nachweise

ORD-Eintrag
ord-4e7d915a5562461fa8c3195f4a254656
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553812B2

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