Iodine → Benzyl 2-(oxazol-2-yl)propan-2-ylcarbamate

HRID 631962Notes

Reaction equation

HRID 631962 reaction equation
[CH3:1][C:2]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:9])[C:3](=[O:8])[NH:4][CH2:5][CH:6]=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.CCN(CC)CC>C(Cl)Cl.O>[O:8]1[CH:6]=[CH:5][N:4]=[C:3]1[C:2]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:9])[CH3:1]

Participants

7

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86674737Benzyl 2-methyl-1-oxo-1-(2-oxoethylamino)propan-2-ylcarbamate

Product 1

HCID 71087227Benzyl 2-(oxazol-2-yl)propan-2-ylcarbamateYield 30.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl 2-methyl-1-oxo-1-(2-oxoethylamino)propan-2-ylcarbamate (2.23 g, 8 mmol) in methylene chloride (50 mL) was added to a freshly prepared solution of PPh3 (3.15 g, 12 mmol), I2 (3.05 g, 12 mmol) and Et3N (2.43 g, 24 mmol) in methylene chloride (100 mL). The resulting mixture was stirred at room temperature until TLC showed the reaction was completed. Then water (150 mL) was added. The organic layer was washed with 5% sodium bisulfite (150 mL×2), brine (150 mL) and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure left a yellow oil which was purified by column chromatography (silica gel, 50 g, eluting with 25% ethyl acetate in petroleum ether) to yield the title compound (0.63 g, 30%) as colorless oil; MS: m/e 261.2 [M+H]+. 1H NMR (300 MHz, CDCl3): δ 7.57 (s, 1H), 7.37-7.33 (m, 5H), 7.05 (s, 1H), 5.06 (s, 2H), 1.74 (s, 6H).

Workup

  1. washThe organic layer was washed with 5% sodium bisulfite (150 mL×2), brine (150 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customRemoval of the solvent under reduced pressure
  4. waitleft a yellow oil which
  5. customwas purified by column chromatography (silica gel, 50 g, eluting with 25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a5f347d47d434398835d714ec9a586d5
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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