Hydrochloric Acid → 2-(3,4-Dichloro-phenylamino)-propionic Acid

HRID 1096191

反応式

HRID 1096191 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12].C1(NN=CC2C=CC=CC=2O)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O.[Cu]I.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][CH:11]([CH3:12])[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 62657Potassium Phosphate, TribasicHCID 88591Benzene, 1,2-dichloro-4-iodo-HCID 2498422-Hydroxybenzaldehyde phenylhydrazone

生成物 1

HCID 69164262-(3,4-Dichloro-phenylamino)-propionic Acid収率 83.9%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3,4-dichloroiodobenzene (1.50 g, 5.50 mmol), L-alanine (734 mg, 8.25 mmol), copper(I) iodide, 2-hydroxybenzaldehyde phenylhydrazone (233 mg, 1.10 mmol), tri-potassium phosphate (3.50 g, 16.5 mmol), and N,N-dimethylformamide (8 mL) was stirred at 80° C. for 40 h, then after cooling diluted with water and acidified to pH 3 by addition of 37% aq. HCl solution. The mixture was extracted with EtOAc, the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc) afforded the title compound (1.08 g, 67%) as a 71:29 mixture of the (S) and (R) stereoisomers (accordingly, when D-alanine was used instead of L-alanine as starting material, the title compound was obtained as a 29:71 mixture of the (S) and (R) stereoisomers). Brown solid, MS: 232.1 (M−H)−.

後処理

  1. temperatureafter cooling
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ba18df7b02184cea8a743c632e8b5caf
出典データセット
uspto-grants-2012_03
特許番号
US08138175B2

関連ノート

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