Iodine → Benzyl [2-(5-ethyloxazol-2-yl)ethyl]carbamate

HRID 1951169Notes

Reaction equation

HRID 1951169 reaction equation
II.C(N(CC)CC)C.[CH2:10]([O:17][C:18](=[O:30])[NH:19][CH2:20][CH2:21][C:22](=[O:29])[NH:23][CH2:24][C:25](=O)[CH2:26][CH3:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([O:17][C:18](=[O:30])[NH:19][CH2:20][CH2:21][C:22]1[O:29][C:25]([CH2:26][CH3:27])=[CH:24][N:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 57637089Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

Product 1

HCID 57636953Benzyl [2-(5-ethyloxazol-2-yl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of polymer supported triphenylphosphene (19.6 g, 58.9 mmol) in DCM (250 ml) is added iodine (14.95 g, 58.9 mmol). After stirring at room temperature for 10 minutes, the mixture is treated with triethylamine (16.4 ml, 117.5 mmol) followed by a solution of [2-(2-Oxo-butylcarbamoyl)-ethyl]-carbamic acid benzyl ester (Step 2) (6.88 g, 23.5 mmol) in DCM (50 ml). The reaction mixture is stirred overnight and then filtered through Celite™ filter material, washed through with DCM (500 ml) and the solvent removed in vacuo to yield the titled compound as a brown solid.

Workup

  1. additionTo a stirred suspension of polymer
  2. stirringThe reaction mixture is stirred overnight
  3. filtrationfiltered through Celite™
  4. filtrationfilter material
  5. washwashed through with DCM (500 ml)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-356966aecbeb4f4c9e3e9915fd31520d
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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