Triethylamine → tert-Butyl (6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1270406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270406
N[CH:2]([NH:10][C:11]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:12]=1C(O)=O)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C>C1(C)C=CC=CC=1>[Br:20][C:18]1[CH:17]=[CH:16][C:12]2[NH:40][C:43](=[O:28])[N:10]([CH2:2][C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[C:11]=2[CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 184493622-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid

Produkt 1

HCID 86607790tert-Butyl (6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid from Step C (2.72 g, 8.24 mmol), diphenylphosphoryl azide (2.1 mL, 9.9 mmol), and triethylamine (1.4 mL, 9.9 mmol) were dissolved in toluene (80 mL) and heated at 100° C. for 1 h. The cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=327 (M+1).

Aufarbeitung

  1. customThe cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-f7783615d34c40889adc1af8c9f100c0
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202251B2

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