1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69739712、化合物

HRID 495815ノート

反応式

HRID 495815 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[S:39]1[CH:43]=[C:42]([CH2:44][CH:45]([NH:62][CH3:63])[C:46]([N:48]([CH3:61])[C@@H:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:47])[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]1=2.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13](=[O:15])[N:62]([C@@H:45]([C:46](=[O:47])[N:48]([CH3:61])[CH:49]([C:57](=[O:60])[NH:58][CH3:59])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:44][C:42]1[C:41]2[CH:64]=[CH:65][CH:66]=[CH:67][C:40]=2[S:39][CH:43]=1)[CH3:63])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 53849785HCID 53849785、化合物

生成物 1

HCID 69739712HCID 69739712、化合物収率 52.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acid (0;19 g; 0.78 mmol) was dissolved in methylene chloride (10 mL). 1-Hydroxy-7-azabenzotriazole (0.11 g; 0.78 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.16 g; 0.86 mmol) were added. The reaction mixture was stirred for 15 min at room temperature. 3-(Benzo[b]thiophen-3-yl)-N-methyl-2-methylamino-N-((1R)-1-methylcarbamoyl-2-phenylethyl)propionamide (0.32 g ; 0.78 mmol) was dissolved in methylene chloride (10 mL) and added. Diisopropylethylamine (0.13 mL; 0.78 mmol) was added. The reaction mixture was stirred for 12 hours at room temperature. Methylene chloride (10 mL) was added. The reaction was washed with water (20 mL), an aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (2×20 cm) using ethylacatate/methylene chloride (1:1) as eluent to afford 0.26 g of ((3E)-4-(((1R)-2-(benzo[b]thiophen-3-yl)-1-(methyl-(1-methylcarbamoyl-2-phenylethyl)carbamoyl)ethyl)methylcarbamoyl)-1,1-dimethylbut-3-enyl)carbamic acid tert-butylester.

後処理

  1. additionadded
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. washThe reaction was washed with water (20 mL)
  4. dry with materialan aqueous solution of sodium hydrogen sulfate (10%; 20 mL), an aqueous solution of sodium hydrogen carbonate (saturated; 20 mL) and dried (magnesium sulfate)
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on silica (2×20 cm)

出典と根拠

ORDレコード
ord-6d9f9a82fdaf4ad3b7ecbf561a3da152
出典データセット
uspto-grants-2005_09
特許番号
US06939880B2

反応ノート

読み込み中…