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

HRID 747705ノート

反応式

HRID 747705 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)butyrate 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 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. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe oily residue was dissolved in 5 ml of dichloromethane
  3. temperatureunder cooling with ice, and they
  4. stirringwere stirred at room temperature overnight
  5. customwhich was purified by the silica gel column chromatography

出典と根拠

ORDレコード
ord-d7ecd08be8d841e3ae21f99f7fd3381e
出典データセット
uspto-grants-2008_07
特許番号
US07396844B1

反応ノート

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