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

HRID 418594

反応式

HRID 418594 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-554b8cb1bf9f44818c74dcf4318dad2f
出典データセット
uspto-grants-2012_01
特許番号
US08093264B2

関連ノート

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