Methyl chloroformate → (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

HRID 1969022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969022
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=1.Cl[C:30]([O:32][CH3:33])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:6]=1

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformate2×HCID 8471Triethylamine2×HCID 58288498{3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester

Produkt 1

HCID 58288472(3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To {3-[2-(benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester (0.076, 0.17 mmol) and methyl chloroformate (0.01 mL, 0.18 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.02 mL, 0.18 mmol), and the reaction was stirred at room temperature for 3 hours. Some starting material was still observed by analytical LCMS, so additional methyl chloroformate (0.02 mL) and triethylamine (0.03 mL) was added, and the reaction was stirred overnight. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred overnight
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography (10-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-537e0e6ff668484faa58e66c9bccbedc
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426449B2

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