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1-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester → 18-(tert-Butyl-dimethyl-silanyloxy)-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 1445423
ノート
印刷プレビュー

反応式

HRID 1445423 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][N:15]2[C:27](=[O:45])[N:28]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]C=C)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:10][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][N:28]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)[C:27](=[O:45])[N:15]1[CH:14]([CH2:18][CH:17]([O:19][Si:20]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:22])[CH3:21])[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 686758741-({4-(tert-Butyl-dimethyl-silanyloxy)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 6687134618-(tert-Butyl-dimethyl-silanyloxy)-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 48%

試薬・触媒・溶媒 2

HCID 11763533
(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium
触媒
HCID 111,2-Dichloroethane溶媒

実験手順

The diene (125) (1 g, 1.6 mmol) was dissolved in degassed DCE (1000 ml), Hoveyda-Grubbs 2nd generation (100 mg, 0.16 mmol) was added and the reaction mixture was refluxed under an atmosphere of argon overnight. The reaction mixture was evaporated on silica and purified by column chromatography on silica gel (30% EtOAc in Heptane→50% EtOAc in Heptane) to give the title compound (470 mg, 0.767 mmol, 48%). M+H=614.

後処理

  1. temperaturethe reaction mixture was refluxed under an atmosphere of argon overnight
  2. customThe reaction mixture was evaporated on silica
  3. custompurified by column chromatography on silica gel (30% EtOAc in Heptane→50% EtOAc in Heptane)

出典と根拠

ORDレコード
ord-8fc42407e7c74690a845e0e973c3ce8f
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07666834B2

反応ノート

読み込み中…

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