Iodine → HCID 44556966, compound

HRID 2236170Notes

Reaction equation

HRID 2236170 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[CH:10]([NH:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:11](=O)[CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C>O1CCCC1>[CH2:1]([O:8][C:9]([C:10]1[N:16]=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:24][C:11]=1[CH:12]([CH3:14])[CH3:13])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 16070893N-Benzoyl-3-oxoleucine phenylmethyl ester

Product 1

HCID 44556966HCID 44556966, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mixture of 2-benzoylamino-4-methyl-3-oxo-pentanoic acid benzyl ester (1.08 g, 3 mmol), triphenylphosphine (2.01 g, 8 mmol), and iodine (1.62 g, 6.37 mmol) in tetrahydrofuran (60 mL) was cooled to −78 degrees, followed by addition of triethylamine (1.7 mL). The resulted solution was stirred at −78 degrees for about 10 min, and then was warmed up to room temperature. The reaction continued at room temperature for about 1 hr. After the reaction, the solvent was removed, and dichloromethane was added. The resulted solution was washed in sequence with saturated sodium bicarbonate, citric acid (0.5 M), and brine, dried over sodium sulfate, filtered and then concentrated in vacuo. Flash chromatography (Merck silica gel 60, 230-400 mesh, 0-40% ethyl acetate in hexane for 20 min) gave 5-isopropyl-2-phenyl-oxazole-4-carboxylic acid benzyl ester (0.84 g, 82%) as a light yellow solid. LCMS calcd for C20H19NO3 (m/e) 321, obsd 322 (M+H).

Workup

  1. temperaturewas cooled to −78 degrees
  2. waitThe reaction continued at room temperature for about 1 hr
  3. customAfter the reaction
  4. customthe solvent was removed
  5. additiondichloromethane was added
  6. washThe resulted solution was washed in sequence with saturated sodium bicarbonate, citric acid (0.5 M), and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15d4a0b6b7c44607ab317e46d4ec6787
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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