Water → (S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester

HRID 1261828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261828
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([N:6]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7][CH:8](OC)[O:9]C)[CH3:5].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CC(=O)CC>[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([N:6]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:7][CH:8]=[O:9])[CH3:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67074039(S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester

Produkt 1

HCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of (S)-2-[benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester (2.94 g, 9.04 mmol) and pyridinium toluene-4-sulfonate (1.13 g, 4.52 mmol) in 2-butanone (30 mL) and water (8.6 mL, 54 mmol) was heated under reflux for 16 h, then the solution was partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (2.45 g, 97%). Yellow oil, MS (ISP)=348.3 (M+Na)+.

Aufarbeitung

  1. temperatureunder reflux for 16 h
  2. customthe solution was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7feb1caccd0c4c39bef30c63d994850e
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471004B2

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