Pyridinium hydrochloride → HCID 178523870, compound

HRID 2294731Notes

Reaction equation

HRID 2294731 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][N:36](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:37]=1)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20])=[O:15])=[O:11].Cl.[NH+]1C=CC=CC=1>CO>[CH:26]1([CH2:25][C@H:17]([NH:16][C:14]([C@@H:13]([NH:12][C:10]([C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)=[O:11])[CH2:32][C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)=[O:15])[C@@H:18]([OH:24])[C@H:19]([CH:21]2[CH2:22][CH2:23]2)[OH:20])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 67930966HCID 67930966, compound

Product 1

HCID 178523870HCID 178523870, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 375 mg (0.39 mmol) of (S)-α-2-benzimidazolecarboxamido-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-tritylimidazole-4-propionamide and 1.8 g (15.6 mmol) of pyridinium hydrochloride in 40 ml of methanol is heated to reflux for 3.5 hours. Thereafter, the reaction mixture is evaporated and the residue is partitioned between 100 ml of ethyl acetate and 50 ml of water. The organic phase is washed with 100 ml of semi-saturated ammonium chloride solution and 100 ml of 2N potassium bicarbonate solution, thereafter dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on 40 g of silica gel using a 6:1 mixture of methylene chloride and methanol as the eluent. There are obtained 110 mg of N-[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]-2-benzimidazolecarboxamide as an amorphous solid; MS: 509 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3.5 hours
  3. customThereafter, the reaction mixture is evaporated
  4. customthe residue is partitioned between 100 ml of ethyl acetate and 50 ml of water
  5. washThe organic phase is washed with 100 ml of semi-saturated ammonium chloride solution and 100 ml of 2N potassium bicarbonate solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated under reduced pressure
  8. customFor purification
  9. customthe residue is chromatographed on 40 g of silica gel using
  10. additiona 6:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-67879736a3ce428781c5c3b154636aa0
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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