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

HRID 1080557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080557
[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-397472edb4ab4763b6cf9a0f58fa4a53
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580896

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