Imidazole → HCID 67490755, compound

HRID 1917329Notes

Reaction equation

HRID 1917329 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH2:27]([O:29][C:30]([CH:32]1[C:36](=[O:37])[N:35]([C@H:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH3:39])[CH2:34][C@H:33]1[C:46]1([CH2:49]O)[CH2:48][CH2:47]1)=[O:31])[CH3:28]>ClCCl>[CH2:27]([O:29][C:30]([CH:32]1[C:36](=[O:37])[N:35]([C@H:38]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH3:39])[CH2:34][C@H:33]1[C:46]1([CH2:49][I:25])[CH2:48][CH2:47]1)=[O:31])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 67490975HCID 67490975, compound

Product 1

HCID 67490755HCID 67490755, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (708 mg, 10.40 mmol), triphenylphosphine (2.727 g, 10.40 mmol), and iodine (2.111 g, 8.32 mmol) were sequentially added to a solution of (3R)-3-[1-(hydroxymethyl)cyclopropan-1-yl]-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidin-4-ylcarboxylic acid ethyl ester (1.378 g, 4.16 mmol) in dichloromethane (50 mL) at room temperature. The mixture was stirred at room temperature for 15 hours. The solvent was evaporated under reduced pressure. Then, the residue was dissolved in ethyl acetate (200 mL) and washed with water (50 mL×2) and brine (50 mL). After drying over anhydrous sodium sulfate and filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9→1:4→1:2) to give 1.606 g (88%) of the title compound as a pale yellow gummy solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThen, the residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with water (50 mL×2) and brine (50 mL)
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9→1:4→1:2)

Sources & evidence

ORD record
ord-34443b1038804056950faa719122d92f
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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