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

HRID 1488686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488686
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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, 3 JHH =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, 3JHH =5 Hz, NCH3), 2.64 (2H, t, 3 JHH =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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-24d72b94ad914f5498611c90857b1c89
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674863

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