Guanidine Hydrochloride → HCID 178513101, compound

HRID 1725176Notes

Reaction equation

HRID 1725176 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC[O-].[Na+].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH2:15][C:16]1[N:17]([CH2:27][C:28](OC(C)(C)C)=[O:29])[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:20]=1>CO>[NH2:4][C:3](=[NH:5])[NH:2][C:28](=[O:29])[CH2:27][N:17]1[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:19][CH:20]=[C:16]1[CH2:15][C:11]1[O:10][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2723922Sodium ethoxideHCID 86607187HCID 86607187, compound

Product 1

HCID 178513101HCID 178513101, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of guanidine hydrochloride in anhydrous MeOH (1.5 ml) was added powder NaOEt (80 mg. 1.17 mmol). After 10 min stirring at room temperature, the reaction mixture was treated with tert-butyl [2-(2-furylmethyl)-5-phenyl-1H-pyrrol-1-yl]acetate. After 5 h stirring at 55° C., the reaction mixture was cooled and quenched with H2O (5 ml), diluted with EtOAc (15 ml). The organic layer was separated and the aqueous was extracted with EtOAc (2×15 ml). The combined organic extracts were washed with H2O (15 ml), brine (15 ml), dried (Na2SO4) and concentrated. The crude material was purified by chromatography (silica gel; EtOAc/2M NH3 in MeOH: 97/3) to give the titled compound (73 mg, 57%) as a solid: mp 80-82° C.; MS (−) ES, 321 (M−H)−.

Workup

  1. stirringAfter 5 h stirring at 55° C.
  2. temperaturethe reaction mixture was cooled
  3. customquenched with H2O (5 ml)
  4. additiondiluted with EtOAc (15 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous was extracted with EtOAc (2×15 ml)
  7. washThe combined organic extracts were washed with H2O (15 ml), brine (15 ml)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude material was purified by chromatography (silica gel; EtOAc/2M NH3 in MeOH: 97/3)

Sources & evidence

ORD record
ord-1717e5acb8024c68ad19993ae06c43f9
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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