Formic Acid → 2-(S)-ethoxy-3-(4-{2-[4-(formylamino)phenyl]ethoxy}-phenyl)propanoic acid ethyl ester

HRID 987318ノート

反応式

HRID 987318 の反応式
[CH:1](O)=[O:2].N1C=CN=C1.C(N(CC)CC)C.C(Cl)(=O)C(Cl)=O.Cl.[CH2:23]([O:25][C:26](=[O:48])[C@@H:27]([O:45][CH2:46][CH3:47])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=2)=[CH:31][CH:30]=1)[CH3:24]>ClCCl.C(OCC)(=O)C.CCCCCCC.O>[CH2:23]([O:25][C:26](=[O:48])[C@@H:27]([O:45][CH2:46][CH3:47])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([NH:44][CH:1]=[O:2])=[CH:42][CH:43]=2)=[CH:31][CH:30]=1)[CH3:24]

参加物

9

反応物 5

HCID 284Formic AcidHCID 795ImidazoleHCID 8471Triethylamine2 回HCID 65578Oxalyl chlorideHCID 86595066HCID 86595066、化合物

生成物 1

HCID 544253382-(S)-ethoxy-3-(4-{2-[4-(formylamino)phenyl]ethoxy}-phenyl)propanoic acid ethyl ester収率 47%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 21899848Ethylacetate heptane溶媒

実験手順

Formic acid (0.0585 g, 1.27 mmole) was dissolved in dichloromethane (2 ml). Imidazole (0.0874 g; 1.27 mmole) was added into the solution, followed by addition of triethylamine (0.353 ml, 2.54 mmole). The mixture was stirred for a little while and then oxalyl chloride (0.161 g; 1.27 mmole) in dichloromethane (2 ml) was added slowly. The resulting mixture was stirred for 30 minutes. A mixture of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester hydro chloride (described in Example 41b) (0.5 g, 1.27 mmole) and triethylamine (0.176 ml; 1.27 mmole) in dichloromethane (3 ml) was added into the reaction mixture. The reaction mixture was stirred at room temperature overnight. Water was added and the phases were separated. The organic phase was washed with water, dried with magnesium sulfate and the solvent was evaporated. Chromatography of the residue on silica gel (isolute, SI) using heptane, then ethyl acetate/heptane (5%), followed by ethyl acetate/heptane (10%) and then ethyl acetate/heptane (25%) as eluants gave 0.230 g (47% yield) of 2-(S)-ethoxy-3-(4-{2-[4-(formylamino)phenyl]ethoxy}-phenyl)propanoic acid ethyl ester.

後処理

  1. stirringThe resulting mixture was stirred for 30 minutes
  2. additionwas added into the reaction mixture
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customthe phases were separated
  5. washThe organic phase was washed with water
  6. dry with materialdried with magnesium sulfate
  7. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-c96180d15b9b4d29a98d3050ad77cdd1
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

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