Triethylamine → 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-propionic acid ethyl ester

HRID 1789840ノート

反応式

HRID 1789840 の反応式
[CH2:1](N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:37])[C:12]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:19][C:20]=1[CH3:21])=[CH2:13])[CH3:9].C(OCC)(=O)C.[C:44]([OH:47])(=[S:46])[CH3:45]>>[CH2:8]([O:10][C:11](=[O:37])[CH:12]([CH2:13][S:46][C:44](=[O:47])[CH3:45])[CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])[C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])=[C:19]([CH3:1])[CH:20]=1)[CH3:9].[CH2:8]([O:10][C:11](=[O:37])[CH:12]([CH2:13][S:46][C:44](=[O:47])[CH3:45])[CH2:14][C:15]1[CH:16]=[N:17][C:18]([N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:19][C:20]=1[CH3:21])[CH3:9]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 539435542-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl esterHCID 178418634HCID 178418634、化合物

生成物 2

HCID 542211002-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-propionic acid ethyl ester収率 21%HCID 570945672-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester

実験手順

Triethylamine (0.279 mL, 2.0 mmol) was added to a solution of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.8 g, 1.9 mmol) in thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was washed with water, saturated NaHCO3 and brine and dried. The crude product was purified by flash chromatography (toluene/ethyl acetate, 3:1→1:2) to give pure 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-propionic acid ethyl ester (200 mg, 21%) and slightly impure 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester (0.68 g).

後処理

  1. washthe organic phase was washed with water, saturated NaHCO3 and brine
  2. customdried
  3. customThe crude product was purified by flash chromatography (toluene/ethyl acetate, 3:1→1:2)

出典と根拠

ORDレコード
ord-85be6c3d5cf947ad8578ebfa34a63d26
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

読み込み中…