Benzyl chloroformate → (2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

HRID 1072942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072942
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:6][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Komponenten

6

Edukt 2

HCID 10387Benzyl chloroformateHCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

Produkt 1

HCID 22865499(2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (2R,3S)-β-phenyl isoserine methyl ester (2) (Preparation No. 1, 2 mM) in pyridine containing a small amount of DMAP is cooled in an ice bath and treated with benzyl chloroformate (0.8 ml). After stirring at room temperature overnight, the reaction is diluted with ethyl acetate, washed with 5% aqueous sodium bisulfate, dried and evaporated. The product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures. Mp 120-121° C. NMR(CDCl3, TMS): δ 3.26 (m, 1H); 3.79 (s, 3H); 4.47 (m, 1H); 5.06 (m, 2H); 5.27 (d, 1H); 5.75 (m, 1H); 7.20-7.50 (m, 10 H).

Aufarbeitung

  1. washwashed with 5% aqueous sodium bisulfate
  2. customdried
  3. customevaporated
  4. customThe product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-2f9dbe92f7f1490f862f9fc257fd589a
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911549B1

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