Triethylamine → benzyl (3R)-3-(4-cyanobenzoylamino)-4-(3-cyanophenoxy)butanoate

HRID 747748ノート

反応式

HRID 747748 の反応式
C(O[C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.[C:31]([C:33]1[CH:41]=[CH:40][C:36](C(Cl)=O)=[CH:35][CH:34]=1)#[N:32].C(N(CC)CC)C.C(OCC)(=O)C>Cl.O1CCOCC1>[C:31]([C:33]1[CH:41]=[CH:40][C:36]([C:6]([NH:8][C@@H:9]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:7])=[CH:35][CH:34]=1)#[N:32]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 801724-Cyanobenzoyl chlorideHCID 10960575benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butyrate

生成物 1

HCID 11761964benzyl (3R)-3-(4-cyanobenzoylamino)-4-(3-cyanophenoxy)butanoate

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

1.8 g (4.38 mmol) of benzyl (3R)-3-t-butoxycarbonylamino-4-(3-cyanophenoxy)butanoate was dissolved in 20 ml of 4 N solution of hydrogen chloride in dioxane, and the solution was stirred at 0° C. for 6 hours. The solvent was evaporated, and the obtained oily residue was dissolved in 5 ml of dichloromethane. 1.09 g (6.58 mmol) of 4-cyanobenzoyl chloride and 1.22 ml (8.76 mmol) of triethylamine were added to the solution under cooling with ice, and they were stirred at room temperature overnight. The reaction mixture was treated with ethyl acetate as the extractant in an ordinary manner to obtain the crude product. After the silica gel column chromatography, the title compound was obtained.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe obtained oily residue was dissolved in 5 ml of dichloromethane
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred at room temperature overnight
  5. customto obtain the crude product

出典と根拠

ORDレコード
ord-acf173b28bb543d1902de9ea09a112c9
出典データセット
uspto-grants-2008_07
特許番号
US07396844B1

反応ノート

読み込み中…