Lithium Hydroxide → 3-(Methyl(phenyl)amino)-3-oxopropanoic acid

HRID 418594노트

반응식

HRID 418594 반응식
Cl[C:2](=[O:8])[CH2:3][C:4]([O:6]C)=[O:5].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Li+].[OH-]>C(Cl)Cl.O>[CH3:9][N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2](=[O:8])[CH2:3][C:4]([OH:6])=[O:5]

참가 물질

6

반응물 3

HCID 3939Lithium HydroxideHCID 7515N-MethylanilineHCID 123460Methyl malonyl chloride

생성물 1

HCID 3500563-(Methyl(phenyl)amino)-3-oxopropanoic acid수율 93%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 3-chloro-3-oxopropanoate (1 mL, 9.32 mmol) and N-methyl aniline (1.01 mL, 9.32 mmol) in DCM (18.6 mL) was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue (N-methyl-N-phenyl-malonamic acid methyl ester, 2.55 g) was dissolved in THF (9 mL). A solution of LiOH×H2O (0.782 g, 18.64 mmol) in water (9 mL) was added and the mixture stirred for 1 h at room temperature. The THF was removed under reduced pressure and the remaining aqueous solution was acidified with 1N HCl (until pH-3) then extracted with EtOAc. The organic phase was concentrated under reduced pressure to afford the acid 31 (1.67 g, 93% yield) as a brown foam. MS (m/z): 194.0 (M+H).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue (N-methyl-N-phenyl-malonamic acid methyl ester, 2.55 g) was dissolved in THF (9 mL)
  3. customThe THF was removed under reduced pressure
  4. extractionthen extracted with EtOAc
  5. concentrationThe organic phase was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-554b8cb1bf9f44818c74dcf4318dad2f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

반응 노트

불러오는 중…