Iodine → HCID 59200408, compound

HRID 1685318Notes

Reaction equation

HRID 1685318 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.II.CO[C:13](=[O:26])[CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(OCC)C>[OH:26][C:13]([C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1)([C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1)[CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 807IodineHCID 115603-BromotolueneHCID 71033Methyl N-benzyloxycarbonylglycinate

Product 1

HCID 59200408HCID 59200408, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Bromotoluene (0.8 mL, 6.6 mmol) was added to Mg turnings (0.312 g, 13 mmol) in diethyl ether (5 mL) and an iodine crystal was also added. The reaction was stirred for 30 minutes. The solution was then transferred to another flask (via a pipet) to separate from the excess Mg. A solution of carbobenzyloxyglycine methyl ester (0.294 g, 1.32 mmol) in diethyl ether (3 mL) was then added to the solution of the Grignard reagent and the reaction was stirred for 1 hour. The reaction was then quenched with sat. aq ammonium chloride and the aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on Biotage chromatography (10% to 10% ethyl acetate/hexane) to give the title material (0.309 g, 62%) as an oil. 1H NMR (400 MHz, DMSO-d6) δ: 2.26 (6H, s), 3.82 (2H, d, J=5.81 Hz), 4.99 (2H, s), 5.76 (1H, s), 6.79 (1H, t, J=5.56 Hz), 7.01 (2H, d, J=7.07 Hz), 7.09-7.40 (11H, m). LC/MS (M−H)−: 374. HPLC ret. time (Condition B): 2.133 min.

Workup

  1. customThe solution was then transferred to another flask
  2. custom(via a pipet) to separate from the excess Mg
  3. stirringthe reaction was stirred for 1 hour
  4. customThe reaction was then quenched with sat. aq ammonium chloride
  5. extractionthe aqueous phase was extracted with ethyl acetate (3×)
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on Biotage chromatography (10% to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a0ee2372e2e6452babda052d02c5ab73
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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