Hydrochloric Acid → 2-(Phenylamino)propanoic acid

HRID 900633

反応式

HRID 900633 の反応式
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C=O)C.C(OCC)(=O)C.O.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl.[Cu]I.CCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(N(CC)CC)C>[C:8]1([NH:1][CH:2]([CH3:3])[C:4]([OH:6])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

13

反応物 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 11430Potassium CarbonateHCID 11575Iodobenzene

生成物 1

HCID 27603572-(Phenylamino)propanoic acid収率 45.4%

試薬・触媒・溶媒 8

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 66133Benzyl triethylammonium chloride触媒HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) Dichloride触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒HCID 21901998Ethyl acetate hexane acetic acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of alanine (356 mg, 4.0 mmol), iodobenzene (816 mg, 4.0 mmol), trans-dichlorobis(tri-o-tolylphosphine)palladium(II) {Pd[P(o-Tol)3]2Cl2} (160 mg, 0.2 mmol), copper(I) iodide (40 mg, 0.2 mmol), K2CO3 (552 mg, 4.0 mmol), benzyltriethylammonium chloride (160 mg, 0.8 mmol), triethylamine (1.6 mL) and water (0.8 mL) in DMF (8 mL) was stirred under nitrogen atmosphere at 100° C. for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and water (50 mL), acidified with 6N HCl to the pH=2 to 3. The aqueous layer was extracted with ethyl acetate (50 mL×4). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a red oil. Flash chromatography using hexane/ethyl acetate/acetic acid (95/5/0.5 to 80/20/0.5) to afford 300 mg (45% yield) of the title compound as a pink solid. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 ml/3 drops) δ 1.45 (d, 3H), 4.02-4.15 (m, H), 6.57-6.70 (m, 3H), 7.11-7.25 (m, 2H); Analytical HPLC: 6.10 min. LC-MS: m/e=166 (M+H+).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×4)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a red oil

出典と根拠

ORDレコード
ord-f521e4f4c0254f28b604189a0262906d
出典データセット
uspto-grants-2008_04
特許番号
US07358273B2

関連ノート

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