Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (S)-ethyl 2-(3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylidene)ethanoate

HRID 75009노트

반응식

HRID 75009 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]2)[C:5]([F:16])=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11](=[CH:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:10]2)[C:5]([F:16])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86667417(S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanone

생성물 1

HCID 86667443(S)-ethyl 2-(3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylidene)ethanoate수율 99.8%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone (29b) (2.00 g, 8.21 mmol) in toluene (40 mL) was added ethyl 2-triphenylphosphoranylideneacetate (4.29 g, 12.31 mmol). The reaction was refluxed overnight then concentrated in vacuo and purified by silica gel chromatography (Hexanes:EtOAc). The desired product eluted at 15% ethyl acetate. Clean fractions were combined and concentrated to give 2.57 g of 62a. LCMS+: 314.18 at 3.75 min (10-90% MeOH, 3/5 grad/run, Formic Acid).

후처리

  1. temperatureThe reaction was refluxed overnight
  2. concentrationthen concentrated in vacuo
  3. custompurified by silica gel chromatography (Hexanes:EtOAc)
  4. washThe desired product eluted at 15% ethyl acetate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-606491bcd3d044b0bb35d5a24fed6259
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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