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4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester → 18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

HRID 1429126
ノート
印刷プレビュー

反応式

HRID 1429126 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[N:18]([C:19](=[O:37])[N:20]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:17][CH:16]([O:38]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:15]2)=[O:13])[CH2:8][CH:7]1C=C)=[O:5])[CH3:2]>ClCCCl>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][N:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:19](=[O:37])[N:18]1[CH:14]([CH2:15][CH:16]([OH:38])[CH2:17]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 668705064-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester

生成物 1

HCID 6687090918-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester収率 61%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
0 °C

実験手順

Compound 2a (1 g, 1.48 mmol) was dissolved in 1,2-dichloroethane (2 l). The mixture was degassed for 15 min using a stream of argon. Hoveyda-Grubbs catalyst (II) (50 mg, 5 mol %) was added and the mixture was refluxed for 4 h. The solvent was evaporated and the crude ester was dissolved in THF (100 ml), methanol (50 ml) and water (50 ml). The mixture was cooled to 0° C. on an ice-bath. Aqueous lithium hydroxide (20 ml, 1M) was added and the mixture was stirred at 0° C. for 4 h. The volume was then doubled by addition of water and the mixture was acidified with acetic acid. Extraction (dichloromethane) followed by flash column chromatography (methanol 1→5% in ether) gave pure title compound (450 mg, 61%).

後処理

  1. customThe mixture was degassed for 15 min
  2. additionHoveyda-Grubbs catalyst (II) (50 mg, 5 mol %) was added
  3. temperaturethe mixture was refluxed for 4 h
  4. customThe solvent was evaporated
  5. dissolutionthe crude ester was dissolved in THF (100 ml)
  6. additionAqueous lithium hydroxide (20 ml, 1M) was added
  7. additionThe volume was then doubled by addition of water
  8. extractionExtraction (dichloromethane)

出典と根拠

ORDレコード
ord-33adbe3f4fdc4dd9b13ee2b38724cd70
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08937080B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート