Methanol → (2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

HRID 1783438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783438
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([OH:18])=[O:17])=[N+:2]=[N-:3].CO.[CH2:21]1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([O:18][CH3:21])=[O:17])=[N+:2]=[N-:3]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 13712291(2S,3R)-1-t-butyldimethylsilyl-3-azido-4-oxo-2-azetidinecarboxylic acid

Produkt 1

HCID 57589884(2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of crude 131 (1.58 g) in CH2Cl2 (25 mL) was added methanol (0.26 mL, 6.43 mmol). DCC (1.45 g, 7.02 mmol) and catalytic DMAP. The solution was stirred at room temperature overnight. The solution was then filtered through Celite and concentrated in vacuo. The crude product was purified by silica gel column chromatography, eluting with 20% EtOAc in hexanes, to yield pure 132.

Aufarbeitung

  1. filtrationThe solution was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by silica gel column chromatography
  4. washeluting with 20% EtOAc in hexanes
  5. customto yield pure 132

Quellen und Nachweise

ORD-Eintrag
ord-635b4696e07342a98a906857c2e01f9a
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501404B2

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