Triethylamine → 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl ester

HRID 1789914ノート

反応式

HRID 1789914 の反応式
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:35])[C:12]([CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:13])[CH3:9].C(OCC)(=O)C.[C:42]([OH:45])(=[S:44])[CH3:43]>>[CH2:8]([O:10][C:11](=[O:35])[CH:12]([CH2:13][S:44][C:42](=[O:45])[CH3:43])[CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:9]

参加物

5

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 537546282-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl esterHCID 178418634HCID 178418634、化合物

生成物 1

HCID 539704052-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl ester収率 73%

反応条件

温度
45 °C

実験手順

Triethylamine (0.105 g, 1.04 mmol) was added to a solution of 2-[(6tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester (0.36 g, 0.94 mmol) in thioacetic acid (4 mL) at 0° C. under argon. The mixture was heated at 45° C. for 24 h. Ethyl acetate was added and the organic phase was washed with aqueous saturated sodium bicarbonate and brine and dried. After filtration and evaporation in vacuo the crude product was purified by flash chromatography (toluene/ethyl acetate, 1:0→5:1) to give 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (0.314 g, 73%).

後処理

  1. washthe organic phase was washed with aqueous saturated sodium bicarbonate and brine
  2. customdried
  3. filtrationAfter filtration and evaporation in vacuo the crude product
  4. customwas purified by flash chromatography (toluene/ethyl acetate, 1:0→5:1)

出典と根拠

ORDレコード
ord-7ff9aa4d50ed477f91ea9ca5941afd61
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

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