HCID 86717460、化合物 → HCID 86717461、化合物

HRID 712001ノート

反応式

HRID 712001 の反応式
[C:1]([O:4][CH2:5][CH:6]([O:9][CH2:10][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH2:13])C=C)(=[O:3])[CH3:2]>C(=[Ru](Cl)(Cl)([C-]1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH:6]1[CH:13]=[CH:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10][O:9]1)(=[O:3])[CH3:2]

参加物

3

反応物 1

HCID 86717460HCID 86717460、化合物

生成物 1

HCID 86717461HCID 86717461、化合物収率 85.4%

試薬・触媒・溶媒 1

HCID 178425457HCID 178425457、化合物触媒

実験手順

To a 500 mL 2-neck round bottom flask, benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)ruthenium (38 mg, 0.044 mmol) was added. After purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL) was added followed by 2-({(2S)-2-[(tert-butoxycarbonyl)amino]but-3-en-1-yl}oxy)but-3-en-1-yl acetate (265 mg, 0.885 mmol). The reaction mixture was stirred at room temperature for 15 h. The mixture was concentrated in vacuo. The residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes) to give the desired product as a brown oil (0.205 g, 85%). LCMS calculated for C9H14NO5 (M+H-Bu+H)+: m/z=216.1. Found: 216.1. 1H NMR (300 MHz, CDCl3) δ 5.94 (0.17H, m), 5.84 (0.83H, m), 5.69 (1H, m), 4.89 (0.13H, m), 4.70 (0.83H, m), 4.25 (1H, m), 4.05 (4H, m), 3.56 (0.13H, m), 3.38 (0.87H, m), 2.04 (2.49H, s), 2.03 (0.51H, m), 1.38 (9H, s) ppm (The product was a ˜5:1 mixture of trans- and cis-isomers).

後処理

  1. customAfter purged with nitrogen for 3 times, dichloromethane (anhydrous, 8 mL)
  2. additionwas added
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified via flash chromatography (eluting with hexanes to 25% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-acec4cde13654fb68ae2fa049c74920e
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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