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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
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HRID 1429126 반응식
[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]
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참가 물질

3

반응물 1

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

생성물 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 ester수율 61%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-33adbe3f4fdc4dd9b13ee2b38724cd70
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937080B2

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