Allyltributylstannane → (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-propenyl)benzenepropanoic acid methyl ester

HRID 1647051노트

반응식

HRID 1647051 반응식
[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](OS(C(F)(F)F)(=O)=O)=[CH:8][CH:7]=1.[CH2:29]([Sn](CCCC)(CCCC)CCCC)[CH:30]=[CH2:31].[Cl-].[Li+]>CN(C)C=O.CCOCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:31][CH:30]=[CH2:29])=[CH:8][CH:7]=1

참가 물질

7

반응물 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 10455198Boc-L-Tyr(Tf)-OMe

생성물 1

HCID 14560595(S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-propenyl)benzenepropanoic acid methyl ester수율 92.2%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Argon was passed through a solution of 7.0 g (0.0164 mol) of (S)-4-[[(trifluoromethyl)sulfonyl]oxy]-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]benzenepropanoic acid methyl ester, 5.7 g (0.0165 mol) of allyltributyl tin, and 1.42 g (0.04 mol) of lithium chloride in 50 mL of dimethylformamide for 10 minutes and 210 mg (0.0003 mol) of bis(triphenylphosphine)palladium dichloride was added. The bath temperature was raised to 90°-95° C. for 40 minutes and the mixture was allowed to cool. The mixture was diluted with ether and washed with water and saturated sodium chloride solution and dried over magnesium sulfate. The residue obtained after filtration and evaporation was purified by preparative liquid chromatography using silica gel cartridges on a Waters Prep 500 chromatograph, eluting with 10% ethyl acetate-hexane to give 4.83 g (92%) of (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(2-propenyl)benzenepropanoic acid methyl ester, mp 56°-59° C.

후처리

  1. temperatureThe bath temperature was raised to 90°-95° C. for 40 minutes
  2. temperatureto cool
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe residue obtained
  6. filtrationafter filtration and evaporation
  7. customwas purified by preparative liquid chromatography
  8. washeluting with 10% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-1c816460925248ef87fa616991b43e9c
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182263

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