(S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate → HCID 58348121, 화합물

HRID 41072

반응식

HRID 41072 반응식
[C:1]([O:7][C@H:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:9][NH:10][C:11]([C@@H:13]([CH2:22][CH:23]=[CH2:24])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:12])(=[O:6])[CH2:2][CH2:3]C=C>C1(C)C=CC=CC=1.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.C(Cl)Cl>[O:12]=[C:11]1[C@H:13]([CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:22][CH:23]=[CH:24][CH2:3][CH2:2][C:1](=[O:6])[O:7][C@H:8]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][NH:10]1

참가 물질

5

반응물 1

HCID 67310751(S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate

생성물 1

HCID 58348121HCID 58348121, 화합물수율 73.1%

시약·촉매·용매 3

HCID 178425456HCID 178425456, 화합물촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

반응 조건

온도
65 °C

실험 절차

To a solution of (S)-tert-butyl 3-((R)-2-(pent-4-enoyloxy)-2-phenylethylcarbamoyl)hex-5-enoate (470 mg, 1.13 mmol) in toluene (113 mL) was added Grubbs 2nd Generation catalyst (96 mg, 0.113 mmol) and the reaction mixture was heated to 65° C. Upon stirring 7 h with continued heating, TLC analysis indicated complete consumption of starting material. The reaction mixture was cooled to rt, diluted with degassed CH2Cl2 (11 ml) and Pb(OAc)4 (251 mg, 0.566 mmol) was added. The resulting mixture was stirred for 12 h at which point the mixture was passed through a short plug of silica then concentrated using rotary evaporation. The resulting purple solid was triturated with methanol to further remove ruthenium complexes. The off white solid that remained was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 320 mg of desired product as a white solid in 73% yield. LRMS (M+Na)+: 410.4.

후처리

  1. customconsumption of starting material
  2. temperatureThe reaction mixture was cooled to rt
  3. additionwas added
  4. stirringThe resulting mixture was stirred for 12 h at which point the mixture
  5. concentrationthen concentrated
  6. customevaporation
  7. customThe resulting purple solid was triturated with methanol to further remove ruthenium complexes
  8. customThe off white solid that remained was purified

출처 및 근거

ORD 기록
ord-50a922f66a094ce8839cea4ea75ace99
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530456B2

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