Ethyl Acetate → (2S,5S)-1-tert-butyl 4-methyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1,4(2H)-dicarboxylate

HRID 627141

반응식

HRID 627141 반응식
[C:1]([O:5][C:6]([N:8]([C@@H:18]([CH:28]=C)[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:9][CH:10]([OH:17])[C:11](=C)[C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>C1(C)C=CC=CC=1.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>[Si:21]([O:20][CH2:19][C@@H:18]1[CH:28]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C@H:10]([OH:17])[CH2:9][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])([C:24]([CH3:26])([CH3:27])[CH3:25])([CH3:22])[CH3:23]

참가 물질

5

반응물 2

HCID 8857Ethyl Acetate2회HCID 89851332methyl 4-(tert-butoxycarbonyl((S)-1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)amino)-3-hydroxy-2-methylenebutanoate2회

생성물 1

HCID 89852366(2S,5S)-1-tert-butyl 4-methyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1,4(2H)-dicarboxylate

시약·촉매·용매 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium촉매HCID 1140Toluene용매

실험 절차

A stirred solution of methyl 4-(tert-butoxycarbonyl((S)-1-(tert-butyldimethylsilyloxy)but-3-en-2-yl)amino)-3-hydroxy-2-methylenebutanoate (Intermediate 100, 16 g, 37 mmol) in toluene (about 300 mL), at ambient temperature in a heat-dried flask, was thoroughly degassed with argon and placed under a nitrogen atmosphere. To this was added Hoveyda-Grubbs Catalyst 2nd Generation (460 mg, 0.74 mmol). Analysis of the mixture 3.5 hours later by LCMS and TLC (15% ethyl acetate in hexanes) indicated very high conversion of starting material to two major products. The reaction mixture was concentrated in vacuo in the presence of enough silica gel to give a free-flowing powder upon reaching dryness. Normal-phase chromatography (0-100% ethyl acetate in hexanes, 330-g column, 45 minutes) was used to isolate the two compounds; the diastereomer shown above (6.4 g, 43%, dark oil) eluted first.

후처리

  1. customAnalysis of the mixture 3.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo in the presence of enough silica gel
  3. customto give a free-flowing powder
  4. customto isolate the two compounds
  5. washeluted first

출처 및 근거

ORD 기록
ord-9b364beaf4cc40a4948a6847af077977
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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