Citric Acid → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

HRID 427364

Reaktionsgleichung

Reaktionsgleichung von HRID 427364
[NH:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[H-].[Na+].CI.[C:19](O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:12][C:11]([O:10][C:8]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][O:4][CH3:19])=[O:9])([CH3:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serine

Produkt 1

HCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a DMF solution containing 2.00 g of Boc-Ser-OH, 0.86 g of sodium hydride (60% oily suspension) was added under ice cooling and the resultant mixture was stirred for 30 min. To the resultant solution, 0.72 ml of methyl iodide was added and the resultant solution was stirred for 3 hr. The reaction mixture was neutralized with citric acid and evaporated under reduced pressure. The obtained residue was redissolved in ethyl acetate, and the solution was washed with 5% aqueous citric acid solution and saturated aqueous sodium chloride solution. successively, and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography (chloroform:methanol=10:1) and crystallized as its DCHA salt from n-hexane to give 0.79 g of the title compound.

Aufarbeitung

  1. additionwas added under ice cooling
  2. customevaporated under reduced pressure
  3. dissolutionThe obtained residue was redissolved in ethyl acetate
  4. washthe solution was washed with 5% aqueous citric acid solution and saturated aqueous sodium chloride solution
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. customThe dried solution was evaporated under reduced pressure
  7. customcrystallized as its DCHA salt from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-896f4f68ddd74fc385c1ace3d6b70b1f
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313094B1

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