Ethyl Acetate → alpha-hydroxymethyl-DL-tryptophan methyl ester

HRID 54863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54863
[CH3:1][O:2][C:3](=[O:24])[CH:4]([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[NH:5]COC([Si](C)(C)C)C.[C:25](OCC)(=[O:27])C>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:24])[C:4]([CH2:25][OH:27])([CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[NH2:5]

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 86747504alpha-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

Produkt 1

HCID 19047815alpha-hydroxymethyl-DL-tryptophan methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

α-Trimethylsilylethoxymethyl-DL-tryptophan methyl ester (1.0 g, 2.8 mmol) was stirred for 48 hours at room temperature in trifluoroacetic acid (10 mL). After evaporation of the acid in vacuo, the oily residue was treated with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and evaporated to give an oil. Trituration with ethyl acetate gave 0.45 g (655) of α-hydroxymethyl-DL-tryptophan methyl ester, mp 148°-149° C.

Aufarbeitung

  1. customAfter evaporation of the acid in vacuo
  2. additionthe oily residue was treated with aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-1ee52c7ed71c4d22a92c6a75eb661606
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622983

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