Lithium Chloride → Tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate

HRID 715972

반응식

HRID 715972 반응식
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12](OS(C(F)(F)F)(=O)=O)[C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4].C([Sn](CCCC)(CCCC)[C:31]#[C:32][CH:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])CCC.[Cl-].[Li+]>CN(C)C=O.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][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:12]([C:31]#[C:32][CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:13]=[CH:14][CH:15]=1)=[O:4]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 70984584Tert-butyl 2-tributylstannanylethynylpyrrolidine-1-carboxylate2회HCID 86712118Methyl 2-(2,2-dimethylpropionylamino)-6-trifluoromethanesulfonyloxybenzoate2회

생성물 1

HCID 70982938Tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenylethynyl]-pyrrolidine-1-carboxylate수율 86.7%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
95 °C

실험 절차

A mixture of methyl 2-(2,2-dimethylpropionylamino)-6-trifluoromethanesulfonyloxybenzoate (Intermediate 39, 3.83 g), tert-butyl 2-tributylstannanylethynyl-pyrrolidine-1-carboxylate (Intermediate 41, 5.81 g), bis(triphenylphosphine)palladium(II) dichloride (0.702 g) and lithium chloride (1.28 g) in dimethylformamide (50 mL) was stirred and heated at 95° C. under nitrogen for 1 hour. After cooling, the mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give tert-butyl 2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenylethynyl]-pyrrolidine-1-carboxylate (3.71 g) as a viscous gum.

후처리

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

출처 및 근거

ORD 기록
ord-a95fe76c005a4de5852ca2e20558e15c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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