Ethyl diazoacetate → (S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl ester

HRID 1360166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360166
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>ClC(Cl)C.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:11][C@@H:9]([CH3:10])[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:12])[CH3:20]

Komponenten

5

Edukt 2

HCID 12192Ethyl diazoacetateHCID 11789722N-Boc-(S)-1-amino-2-propanol

Produkt 1

HCID 86621906(S)-(2-t-butoxycarbonylamino-1-methyl-ethoxy)-acetic acid ethyl esterAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 168478Rhodium acetateKatalysatorHCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1.16 g (6.61 mmol) of (S)-(2-hydroxy-propyl)-carbamic acid t-butyl ester was dissolved in 20 mL of dichloroethane, then 0.66 mL (9.84 mmol) of ethyl diazoacetate was added thereto. 57 mg (0.12 mmol) of rhodium acetate was dropwise added thereto, and then heated to at 80° C. for 2 hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 1.2 g (4.59 mmol) of the title compound in a yield of 69%.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb3a68af140f42c8a17e551722efc526
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879848B2

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