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Chemical Structure| 332124-25-1 Chemical Structure| 332124-25-1

Structure of 332124-25-1

Chemical Structure| 332124-25-1

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Product Details of [ 332124-25-1 ]

CAS No. :332124-25-1
Formula : C8H8BrIO
M.W : 326.96
SMILES Code : COC1=CC=C(C(I)=C1)CBr
MDL No. :MFCD18905187

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Application In Synthesis of [ 332124-25-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 332124-25-1 ]

[ 332124-25-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 332124-25-1 ]
  • [ 119838-38-9 ]
  • [ 332124-27-3 ]
YieldReaction ConditionsOperation in experiment
23% a) (2S,5S)-tert-Butyl-5-(2'-iodo-4'-methoxybenzyl)-2-tert-butyl-3-methyl-4- oxoimidazolidine- 1 -carboxylate (27); This product was obtained using the general procedure reported in the literature [(D. Seebach, E. Dziadulewicz, L. Behrendt, S. Cantoreggi, R. Fitzi, "Synthesis of Nonproteinogenic (R)- or (S)-Amnio Acids Analogues of Phenylalanine, Isotopically Labelled and Cyclic Amino Acids from tert-Butyl 2-(tert-Butyl)-3-methyl-4-oxo-l- imidazolidinecarboxylate (Boc-BMI)." Liebigs Ann. Chem., pp 1215-1232 (1989)]. Diisopropylamine (0.9 mL, 6.4 mmol) dissolved in dry THF (5 mL) was cooled to - 78 C under argon and a solution of BuLi (2.5 M in hexane, 2.5 mL) was added drop wise. After 20 min of stirring at -78 C, a solution of (S)-tert-butyl-2-tert-butyl-3- methyl-4-oxoimidazolidine-l -carboxylate (3.0 g, 1 1.9 mmol) was added drop wise and the reaction mixture was stirred for 30 min at - 40 C. A solution of 2-iodo-4- methoxybenzyl bromide (20) (2.08 g, 6.4 mmol) in dry THF (2 mL) was then added drop wise to the reaction mixture. The new reaction mixture was stirred for 2 hours at the same temperature and then poured into a saturated solution of NH4Cl. The product was extracted with EtOAc and the organic layer was washed with NaHCO3 solution followed by brine. The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to produce a yellow oil. Flash chromatographic purification of the oily product provided pure (2S,5S)-tert-Butyl-5-(2'-iodo-4'-methoxybenzyl)-2- tert-butyl-3-methyl-4-oxoimida-zolidine-l-carboxylate (27) as a white solid (743.7 mg, 23%).1H NMR (CDCl3): delta 7.40 (s, IH, H-31), 6.80 (d, 2H, H-5',61), 5.09 (s, IH, H-2), 4.36(dd, IH, H-5), 3.75 (s, 3H, 4'-OCH3), 3.54, 3.40 (dd, 2H, CH2), 3.03 (s, 3H, NCH3),1.33 (s, 9H, NBoc CH3 ), 1.01 (s, 9H, tert-butyl CH3).13C NMR (CDCl3): delta 171.44 (C-4), 157.97 (C-4'), 131.66 (C-I'), 127.65 (C-6?),124.92 (C-3'), 113.97 (C-51), 101.78 (C-21), 81.16 (Boc tert-C), 80.81 (C-5), 58.52 (C-2), 55.45 (4'-OCH3), 40.74 (tert-butyl tert-C), 31.98 (C-7), 28.08 (B0C-CH3, NMe),26.40 (tert-butyl CH3).MS (ESI) Calcd for C2iH3iIN2O4 (M+): 502.13; Found: 503.13 (M++l).Figure 19 shows the C-13/H-1 HMBC NMR spectrum of compound 27.
 

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