Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (R,E)-ethyl 4-((2-chloro-5-fluoropyrimidin-4-yl)amino)-5,5-dimethylhex-2-enoate

HRID 1055048노트

반응식

HRID 1055048 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:10]=O)[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>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:12]([CH3:15])([CH3:14])[CH3:13])/[CH:10]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:5]([F:16])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86714733(S)-2-((2-chloro-5-fluoropyrimidin-4-yl)amino)-3,3-dimethylbutanal2회

생성물 1

HCID 86714739(R,E)-ethyl 4-((2-chloro-5-fluoropyrimidin-4-yl)amino)-5,5-dimethylhex-2-enoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-2-((2-chloro-5-fluoropyrimidin-4-yl)amino)-3,3-dimethylbutanal, 15a, (0.45 g, 1.84 mmol) in dichloromethane (9.0 mL) was added ethyl 2-triphenylphosphoranylideneacetate (0.96 g, 2.75 mmol). After allowing the reaction mixture to stir at room temperature overnight, approximately half of the solvent was removed under reduced pressure. The remaining crude mixture was purified by directly loading onto a silica gel column (0-100% EtOAc/hexanes) to afford 535 mg of the desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, RT=3.41 minutes (M+H) 316.32.

후처리

  1. customapproximately half of the solvent was removed under reduced pressure
  2. customThe remaining crude mixture was purified

출처 및 근거

ORD 기록
ord-01588e087a7c4708a04081656874cf71
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394302B2

반응 노트

불러오는 중…