Triphenylphosphine → HCID 12149962, compound

HRID 394022Notes

Reaction equation

HRID 394022 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:30])[CH2:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:6]([C:31]([N:33]2[CH2:37][CH2:36][CH2:35][C@@H:34]2[C:38]([NH:40][CH2:41][C@H:42]2[CH2:47][CH2:46][CH2:45][N:44]([CH2:48][CH:49]3[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]3)[CH2:43]2)=[O:39])=[O:32])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(Cl)(Cl)Cl>[NH2:1][C@@H:4]1[CH2:8][N:7]([C:9](=[O:30])[CH2:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]([C:31]([N:33]2[CH2:37][CH2:36][CH2:35][C@@H:34]2[C:38]([NH:40][CH2:41][C@H:42]2[CH2:47][CH2:46][CH2:45][N:44]([CH2:48][CH:49]3[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]3)[CH2:43]2)=[O:39])=[O:32])[CH2:5]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 12149963HCID 12149963, compound

Product 1

HCID 12149962HCID 12149962, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 24 mg of (2R)-1-{(2S,4S)-4-azido-1-(3,3,3-triphenyl-propanoyl)pyrrolidin-2-yl}carbonyl-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide in 0.5 ml of 20% hydrous tetrahydrofuran, 13 mg of triphenylphosphine was added at room temperature, followed by 3 hours' refluxing under heating. The reaction liquid was diluted with chloroform, washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resultant residue was purified by means of a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=90/10/1) to provide 16 mg of the title compound in the form of a white solid.

Workup

  1. temperature' refluxing
  2. temperatureunder heating
  3. customThe reaction liquid
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure
  7. customthe resultant residue was purified by means of a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=90/10/1)

Sources & evidence

ORD record
ord-2a33768ceded4befb5db38b3d9d1e241
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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