Ethyl methyl sulfide → 3-Phenyl-2-prop-2-ynylamino-propionic acid methyl ester

HRID 2179932

Reaction equation

HRID 2179932 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]([N:12](S(C1C(C)=CC(OC)=C(C)C=1C)(=O)=O)[CH2:13][C:14]#[CH:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CSCC>ClC(Cl)C.FC(F)(F)C(O)=O>[CH3:1][O:2][C:3](=[O:30])[CH:4]([NH:12][CH2:13][C:14]#[CH:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 12230Ethyl methyl sulfideHCID 207793062-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester

Product 1

HCID 207793083-Phenyl-2-prop-2-ynylamino-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-[(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester (150 mg, 0.349 mmol) in anhydrous dichloroethane (1.5 mL), trifluoroacetic acid (3.5 mL) and ethyl methyl sulfide (0.16 mL, 1.75 mmol) were added. The reaction mixture was stirred at room temperature under a N2 atmosphere for 12 h. Excess of solvents were removed under reduced pressure and the residue was extracted between saturated NaHCO3 solution and ethyl acetate. The organic layer was separated, dried (Na2SO4), concentrated. The crude product was purified by silica gel column chromatography using ethyl acetate and hexane (1:3) as eluent to obtain 3-Phenyl-2-prop-2-ynylamino-propionic acid methyl ester as a thick syrup, 70 mg (92%). 1H NMR (CDCl3, 400 MHz): δ7.32-7.19 (m, 5H), 3.78 (t, 1H), 3.68 (s, 3H), 3.40 (ABq, 2H), 3.03 (dd, 1H), 2.98 (dd, 1H), 1.99 (t, 1H).

Workup

  1. customExcess of solvents were removed under reduced pressure
  2. extractionthe residue was extracted between saturated NaHCO3 solution and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14d2abf5250847349088d3c5a01ad3f0
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Linked notes

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