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

HRID 2179932

반응식

HRID 2179932 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-14d2abf5250847349088d3c5a01ad3f0
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887877B2

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