Methyl iodide → N-(2-methylamino-5-iodobenzoyl)-b-alanine benzyl ester

HRID 1488663노트

반응식

HRID 1488663 반응식
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[CH3:2].N1C(C)=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:26].[CH3:27]I>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([I:15])[CH:12]=[CH:11][C:10]=1[NH:16][CH3:27])[C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:26]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 79372,6-LutidineHCID 10861356N-(2-amino-5-iodobenzoyl)-b-alanine ethyl ester

생성물 1

HCID 22905394N-(2-methylamino-5-iodobenzoyl)-b-alanine benzyl ester수율 35%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A magnetically stirred solution of 0.848 gram of N-(2-amino-5-iodobenzoyl)-b-alanine ethyl ester (2.0 mmol), 0.35 mL 2,6-lutidine (3.0 mmol), 0.19 mL methyl iodide (3.0 mmol), and 15 mL dimethylformamide was heated to 50° C. for 15 hours. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The resulting residue was dissolved in 75 mL ethyl acetate and washed 1×50 mL 10% citric acid, 1×50 mL sat. sodium bicarbonate, 1×50 mL brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was further purified by column chromatography, using silica gel, eluting with a solvent gradient of 35/65 ethyl acetate/hexane to 65/35 ethyl acetate/hexane (TLC, SiO2, 1:1 EtOAc/hexane, Rf =0.84, un positive) to yield 305 mgs (35%) of N-(2-methylamino-5-iodobenzoyl)-b-alanine benzyl ester. 1H NMR (CDCl3, dTMS) 7.56 (2H, m, Ar--H, o,p-CON), 7.43 (1H, bq, 3 JHH=5 Hz, NHMe), 7.38-7.32 (5H, s, ArH Ph), 6.62 (1H, bt, 3JHH=6 Hz, CONH), 6.42 (1H, d, 3JHH=9 Hz, Ar--H m-CON), 5.16 (2H, s, OCH2), 3.64 (2H, q, 3JHH=6 Hz, NCH2), 2.81 (3H, d, 3 JHH=5 Hz, NCH3), 2.64 (2H, t, 3JHH=6 Hz, CH2CO2). 13C NMR (CDCl3, dTMS) 172.4, 168.4, 148.8, 141.0, 135.5, 128.7, 128.4, 117.3, 113.4, 74.1, 66.7, 35.2, 34.0, 29.6.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in 75 mL ethyl acetate
  3. washwashed 1×50 mL 10% citric acid, 1×50 mL sat. sodium bicarbonate, 1×50 mL brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was further purified by column chromatography
  8. washeluting with a solvent gradient of 35/65 ethyl acetate/hexane to 65/35 ethyl acetate/hexane (TLC, SiO2, 1:1 EtOAc/hexane, Rf =0.84, un positive)

출처 및 근거

ORD 기록
ord-12cf924ae1e54c09a9ed002ec3566803
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674865

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