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

HRID 2110924Notes

Reaction equation

HRID 2110924 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.O=[C:30]([CH2:48][CH3:49])[CH2:31][NH:32][C:33]([CH2:35][CH2:36][NH:37][C:38](=[O:47])[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:34]>ClCCl>[CH2:40]([O:39][C:38](=[O:47])[NH:37][CH2:36][CH2:35][C:33]1[O:34][C:30]([CH2:48][CH3:49])=[CH:31][N:32]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57637089Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

23.07 g (49.60 mmol) PS-triphenylphosphine are in 200 ml dichloromethane suspended, 12.65 g (49.82 mmol) iodine are added. It is stirred for 0.1 hours at ambient temperature, then 13.80 ml (99.28 mmol) triethylamine are added dropwise. 5.80 g (19.84 mmol) benzyl [2-(2-oxo-butylcarbamoyl)-ethyl]-carbamate dissolved in 150 ml dichloromethane are added. The reaction mixture is stirred for 72 hours at ambient temperature, then the precipitate is filtered off. The filtrate is extracted with water, the organic phase is dried and evaporated to dryness.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 72 hours at ambient temperature
  3. filtrationthe precipitate is filtered off
  4. extractionThe filtrate is extracted with water
  5. customthe organic phase is dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-66c2f8a0b6ab46e98a1332b04452dee5
Source dataset
uspto-grants-2009_04
Patent number
US07517995B2

Reaction notes

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