Hexane → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 891667

Reaktionsgleichung

Reaktionsgleichung von HRID 891667
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:18][Si](C=[N+]=[N-])(C)C.CCCCCC>C1C=CC=CC=1.CO>[CH3:18][O:16][C:15](=[O:17])[C@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 167693Trimethylsilyldiazomethane

Produkt 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of N-carbobenzyloxy-L-serine (4.0 g, 16.7 mmol) in benzene (200 ml) and methanol (50 ml) was added a solution of 2M trimethylsilyldiazomethane in hexane (10.9 ml, 21.7 mmol) in an ice bath, and the mixture was stirred at room temperature for 3 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:1→1:3) as the eluant to afford N-carbobenzyloxy-L-serine methyl ester (4.40 g, yield 100%) as a colorless oil.

Aufarbeitung

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-4b434369fbc940f9a0701f5badd41222
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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