HCID 86717460, 화합물 → HCID 86717461, 화합물

HRID 712001노트

반응식

HRID 712001 반응식
[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]

참가 물질

3

반응물 1

HCID 86717460HCID 86717460, 화합물

생성물 1

HCID 86717461HCID 86717461, 화합물수율 85.4%

시약·촉매·용매 1

HCID 178425457HCID 178425457, 화합물촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-acec4cde13654fb68ae2fa049c74920e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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