Hydrochloric Acid → 2-(Phenylamino)propanoic acid

HRID 900633

반응식

HRID 900633 반응식
[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

참가 물질

13

반응물 4

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

생성물 1

HCID 27603572-(Phenylamino)propanoic acid수율 45.4%

시약·촉매·용매 8

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 66133Benzyl triethylammonium chloride촉매HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) Dichloride촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매HCID 21901998Ethyl acetate hexane acetic acid용매

반응 조건

온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-f521e4f4c0254f28b604189a0262906d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358273B2

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