Chloroiodomethane → 2,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester

HRID 1170606

Reaktionsgleichung

Reaktionsgleichung von HRID 1170606
[CH3:1][C:2]([CH3:25])([CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:23])[CH3:22])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:3]([OH:5])=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:44][CH2:45]I>O1CCOCC1>[Cl:44][CH2:45][O:4][C:3](=[O:5])[C:2]([CH3:1])([CH3:25])[CH2:6][O:7][C:8](=[O:24])[C@@H:9]([CH:21]([CH3:22])[CH3:23])[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12]

Komponenten

5

Edukt 3

HCID 11644ChloroiodomethaneHCID 2723671Tetrabutylammonium HydroxideHCID 233874902,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid

Produkt 1

HCID 537919342,2-Dimethyl-3-(N-CBz-D-valyloxy)-propionic acid chloromethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(2,2-dimethyl-3-(N-CBz-D-valyloxy)-propionic acid (4.5 g, 12.8 mmole) was dissolved in dioxane (20 ml). To the solution was added tetrabutylammonium hydroxide aqueous solution (40%, 8.3 ml, 12.8 mmole). The solution was dried in vacuo, and it was coevaporated with toluene several times. The residue was dissolved in methylene chloride and then chloroiodomethane (18 ml, 260 mmole) was added to the solution. After 18 hr, the reaction solution was evaporated and the product was isolated with silica gel column chromatography. 3.5 g.

Aufarbeitung

  1. customThe solution was dried in vacuo, and it
  2. dissolutionThe residue was dissolved in methylene chloride
  3. customthe reaction solution was evaporated
  4. customthe product was isolated with silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e728478c0c6f41978e94f4b7a22af884
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825238B2

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