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

HRID 54863Notes

Reaction equation

HRID 54863 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 19047815alpha-hydroxymethyl-DL-tryptophan methyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1ee52c7ed71c4d22a92c6a75eb661606
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Reaction notes

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