HCID 23321921, compound → HCID 12801697, compound

HRID 280113Notes

Reaction equation

HRID 280113 reaction equation
C([O:5][C:6](=[O:24])[CH2:7][N:8]([C:15](=[O:23])[CH:16]([CH3:22])[CH2:17][S:18][C:19](=[O:21])[CH3:20])[CH2:9][C:10]1[O:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[C:19]([S:18][CH2:17][CH:16]([CH3:22])[C:15]([N:8]([CH2:9][C:10]1[O:14][CH:13]=[CH:12][CH:11]=1)[CH2:7][C:6]([OH:24])=[O:5])=[O:23])(=[O:21])[CH3:20]

Participants

4

Reactant 1

HCID 23321921HCID 23321921, compound

Product 1

HCID 12801697HCID 12801697, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Crude N-(3-acetylthio-2-methylpropanoyl)-N-furfurylglycine tert-butyl ester (14.6 g, 0.0407 mol) was dissolved in a mixture of anisole (20 ml) and trifluoroacetic acid (65 ml). The resulting solution was stirred at room temperature for two hours. The solvent was evaporated in vacuo and the residue was distributed between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous bicarbonate extract was washed twice with ethyl acetate and then acidified cautiously with concentrated hydrochloric acid to pH 4-5. The product was extracted several times into chloroform and the chloroform was washed twice with water. The organic phase was dried over magnesium sulfate, filtered and evaporated to give crude product as a pale yellow oil which was purified by HPLC using the following solvent system: ethyl acetate/n-hexane/acetic acid (40:60:1) to give pure product as a colorless oil (5.5 g, 44.7%). The product was purified by its DCHA salt which was prepared in ether, m.p. 140°-141° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionThe aqueous bicarbonate extract
  3. washwas washed twice with ethyl acetate
  4. extractionThe product was extracted several times into chloroform
  5. washthe chloroform was washed twice with water
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude product as a pale yellow oil which
  10. customwas purified by HPLC

Sources & evidence

ORD record
ord-13e700f23b244d0d8da75155375d23b5
Source dataset
uspto-grants-1986_05
Patent number
US04588734

Reaction notes

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