HCID 20285469, compound → HCID 20285476, compound

HRID 127633Notes

Reaction equation

HRID 127633 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])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=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]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:7][C:6]([OH:24])=[O:5])=[O:23])(=[O:21])[CH3:20]

Participants

4

Reactant 1

HCID 20285469HCID 20285469, compound

Product 1

HCID 20285476HCID 20285476, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Crude N-(3-acetylthio-2-methylpropanoyl)-N-phenylglycine tert-butyl ester (25 g, 0.0712 mol) was dissolved in a mixture of anisole (40 ml) and trifluoroacetic acid (125 ml). The resulting red solution was stirred overnight at room temperature. The solvent was evaporated and the residue was distributed between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous sodium bicarbonate layer was acidified cautiously with concentrated hydrochloric acid to pH 4-5. The product was extracted several times into chloroform, washed twice with water, and dried over magnesium sulfate. Filtration and evaporation of the extract afforded the crude product as an orange oil which was further purified by HPLC, eluting with ethyl acetate/n-hexane/acetic acid (40:60:1), to afford pure product (7.5 g., 36%) as a pale yellow oil. The product was crystallized from diethyl ether to afford colorless prisms, m.p. 94°-94.5° C.

Workup

  1. customThe solvent was evaporated
  2. extractionThe product was extracted several times into chloroform
  3. washwashed twice with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and evaporation of the extract

Sources & evidence

ORD record
ord-e330ab17c9394b88b4c1d5dbd47bb717
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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