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

HRID 2179932

反応式

HRID 2179932 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-14d2abf5250847349088d3c5a01ad3f0
出典データセット
uspto-grants-2005_05
特許番号
US06887877B2

関連ノート

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