Benzyl chloroformate → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 366907

Reaktionsgleichung

Reaktionsgleichung von HRID 366907
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[OH-].[Na+]>O>[OH:8][CH2:7][C@H:5]([NH:6][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:4]([O:3][CH3:2])=[O:9]

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 24.01 g L-serine-methylester hydrochloride in 130 ml of water were added at 0° C. 29.8 g of benzyl chloroformate. The pH was kept at 6-7 by adding a 40% aqueous solution of sodium hydroxide. After 3 h at 0° C. the mixture was extracted with 5 portions of ethyl acetate, the combined extracts were dried and evaporated to give 37.12 g (95%) of pure methyl 3-hydroxy-(S)-2-benzyloxycarbonylamino-propionate. IR (neat): 3380 m (NH, OH), 1720 s, br. (C=O), 1540 s (amide II).

Aufarbeitung

  1. extractionAfter 3 h at 0° C. the mixture was extracted with 5 portions of ethyl acetate
  2. customthe combined extracts were dried
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ff11aa4641b54591917c8f0b3a2e812a
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130348

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