Methane, dichloromethoxy- → (2S,5S)-tert-Butyl-5-(2'-iodo-4'-methoxy-5'-formylbenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate

HRID 1188756Notes

Reaction equation

HRID 1188756 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[I:22])[C:11](=[O:23])[N:10]([CH3:24])[C@@H:9]1[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[Sn](Cl)(Cl)Cl.[CH3:34][O:35]C(Cl)Cl>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[C:18]([CH:34]=[O:35])[C:17]([O:20][CH3:21])=[CH:16][C:15]=2[I:22])[C:11](=[O:23])[N:10]([CH3:24])[C@@H:9]1[C:25]([CH3:28])([CH3:27])[CH3:26])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachloride2×HCID 11306634(2S,5S)-tert-Butyl-5-(2'-iodo-4'-methoxybenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate

Product 1

HCID 15907954(2S,5S)-tert-Butyl-5-(2'-iodo-4'-methoxy-5'-formylbenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylateYield 11.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The iodoanisole derivative 27 (460.20 mg, 0.94 mmol) was dissolved in anhydrous dichloromethane (10 mL) and cooled to 0° C. under argon. After stirring for 15 min a solution of SnCl4 (1M in dichloromethane, 10.4 mL, 10.4 mmol) was added drop wise. After completion of the addition of SnCl4, 1,1-dichloromethyl methyl ether (0.84 mL, 9.4 mmol) was added drop wise. The color of the solution turned from light yellow to greenish brown. The reaction mixture was stirred for 45 min at 0° C. and then quenched with a saturated solution of ammonium chloride (2.0 mL). The light brown suspension was stirred for 30 min at room temperature and extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to afford a yellow oil. Flash chromatographic purification of the crude product gave pure (2S,5S)-tert-Butyl-5-(2′-iodo-4′-methoxy-5′-formylbenzyl)-2-tert-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate (28) as oil (57 mg, 10%).

Workup

  1. additionwas added drop wise
  2. additionwas added drop wise
  3. customquenched with a saturated solution of ammonium chloride (2.0 mL)
  4. stirringThe light brown suspension was stirred for 30 min at room temperature
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic phase was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a yellow oil
  10. customFlash chromatographic purification of the crude product

Sources & evidence

ORD record
ord-26757ccd135247ffba1de1fa228903b8
Source dataset
uspto-grants-2014_03
Patent number
US08674101B2

Reaction notes

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