Trityl chloride → N-trityl-t-butyldimethylsilyloxy serine methyl ester

HRID 1734685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734685
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:14][OH:15])[NH:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C.[C:26](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:14][OH:15])[N:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])[C:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

5

Edukt 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 22856314t-Butyldimethylsilyloxyserine methyl ester

Produkt 1

HCID 22856313N-trityl-t-butyldimethylsilyloxy serine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To t-butyldimethylsilyloxyserine methyl ester (27.5 g; 0.118 mol) dissolved in CH2Cl2 (125 ml) and diisopropylethylamine (25 ml; 0.14 mol) and cooled to 0° C. is added tritylchloride (33. g; 0.118 mol) portionwise over 2 minutes. The reaction is stirred for 4 hours at 25° C., diluted with CH2Cl2 and washed with H2O 3x. The organic phase is dried (MgSO4) and concentrated to dryness to give N-trityl-t-butyldimethylsilyloxy serine methyl ester as a tan solid which is used directly next Step C.

Aufarbeitung

  1. washwashed with H2O 3x
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2d3c4202b4bc42989a1aed4f33e8dd29
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534532

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