Triethylamine → HCID 178501369、化合物

HRID 2249977ノート

反応式

HRID 2249977 の反応式
Cl.[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH:22]([C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1)([CH3:24])[CH3:23]>ClC(Cl)C>[CH3:2][O:3][C:4](=[O:14])[C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:31]([C@H:28]1[CH2:29][CH2:30][C@H:25]([CH:22]([CH3:24])[CH3:23])[CH2:26][CH2:27]1)=[O:32]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11481330methyl (2R)-2-amino-3-phenylpropanoate;hydrochlorideHCID 178448099HCID 178448099、化合物

生成物 1

HCID 178501369HCID 178501369、化合物収率 50.8%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

D-Phenylalanine methyl ester hydrochloride (20 g, 0.092 mol) was suspended in a solution of triethylamine (66 mL) in dichloroethane (100 mL) and the mixture was stirred for 1 hour at room temperature. The organic layer was separated after washing with water and dried over anhydrous sodium sulphate. Trans-4-isopropylcyclohexane carboxylic acid (15.8 g, 0.092 mol) was added to the organic layer followed by LiOH—Al2O3 (5.5 g of LiOH adsorbed on 40.5 g aluminum oxide) and the resulting mixture heated at for 24 hours. The reaction mixture was filtered through a celite bed and washed with 1.5 N HCl, 5% sodium bicarbonate solution and brine. The organic layer was concentrated to yield 15.5 g of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine methyl ester.

後処理

  1. customThe organic layer was separated
  2. washafter washing with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. temperaturethe resulting mixture heated at for 24 hours
  5. filtrationThe reaction mixture was filtered through a celite bed
  6. washwashed with 1.5 N HCl, 5% sodium bicarbonate solution and brine
  7. concentrationThe organic layer was concentrated

出典と根拠

ORDレコード
ord-7fe3a0a784d44bc984df5bd0abdf3b36
出典データセット
uspto-grants-2008_01
特許番号
US07314955B2

反応ノート

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