Iodine → 4-[(Benzyloxy)methyl]-5-(iodomethyl)-1,3-oxazolidin-2-one

HRID 595329Notes

Reaction equation

HRID 595329 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1C=CC=CC=1)C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]I>ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH2:1]([O:8][CH2:9][CH:10]1[CH:16]([CH2:17][I:24])[O:15][C:14](=[O:23])[NH:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 12180511Benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate

Product 1

HCID 135674724-[(Benzyloxy)methyl]-5-(iodomethyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate (3.0 g, 9.6 mmol) and iodine (4.9 g, 19 mmol) in dichloromethane (200 mL) was stirred at 20° C. for 16 hours. The reaction mixture was diluted with aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give 4-[(benzyloxy)methyl]-5-(iodomethyl)-1,3-oxazolidin-2-one. MS ESI calc'd. for C12H15INO3 [M+H]+ 348. found 348. 1H NMR (300 MHz, CDCl3) δ 7.40-7.27 (m, 5H), 5.53 (s, 1H), 4.57 (s, 2H), 4.37-4.34 (m, 1H), 3.82-3.80 (m, 1H), 3.67-3.51 (m, 2H), 3.38-3.32 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product residue
  6. customThe crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-3570c4be1b924f539521e5d284cfe153
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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