Reaktion #539303

Reaktionsgleichung

4-(2-(dimethylamino)ethoxy)benzaldehyde

triphenyl phosphonium methyl bromide

t-butyl carbamate

thionyl chloride

4-bromo 1,2-diamino benzene

n-butyl lithium

1,2-diaminocyclohexane

→

(S)-4-(4-(2-(dimethylamino)ethoxy)phenyl)-3-(1H-benzo[d]imidazol-5-yl)oxazolidin-2-one

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe compound was synthesized
2. 2
   Sonstigert 5.79 min (94.7%)

Vorschrift

The compound was synthesized according to method 5 starting from 4-(2-(dimethylamino)ethoxy)benzaldehyde (3 g, 15.70 mmol), 2.3 M n-butyl lithium (13.65 mL, 15.7 mmol), triphenyl phosphonium methyl bromide (11.21 g, 17 mmol) T-butyl hypochlorite (2.7 mL, 22.32 mmol), t-butyl carbamate (2.66 g, 22.72 mmol) 0.4M aqueous sodium hydroxide (0.9 g in 57 mL water), osmate dihydrate (100 mg, 0.29 mmol), thionyl chloride (1.2 mL, 16.49 mmol), 4-bromo 1,2-diamino benzene (0.31 mg, 0.1.672 mmol), and copper iodide (44 mg, 0.228), 1,2-diaminocyclohexane (26 mg, 0.228), formic acid (3 mL). Yield: 0.110 g (2.0%); MS m/z 367.2 (M+H)+; 1H NMR (400 MHz, CDCl3): δ10.40 (Bs, 1H); 7.89 (s, 1H); 7.53 (s, 1H); 7.26-7.19 (merged with CDCl3, 5H); 6.81 (d, 2H); 5.33 (t, 1H); 4.79 (q, 1H); 4.25 (t, 1H); 4.00 (t, 2H); 2.70 (t, 2H); 2.34-2.25 (m, 6H); HPLC (λ=214 nm), [A]: rt 5.79 min (94.7%).

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