Hydrochloric Acid → HCID 54228399, compound

HRID 325936Notes

Reaction equation

HRID 325936 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].[CH3:9][C@H:10]1[CH:14]=[CH:13][C@@H:12]([CH3:15])[N:11]1[CH2:16][C:17](OC)=[O:18].Cl>C(O)(C)C.CO>[NH2:4][C:3]([NH2:5])=[N:2][C:17](=[O:18])[CH2:16][N:11]1[C@H:12]([CH3:15])[CH:13]=[CH:14][C@@H:10]1[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 53672145Methyl [(2R,5S)-2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl]acetate

Product 1

HCID 54228399HCID 54228399, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of guanidine hydrochloride (0.6 g.) sodium methoxide (from 0.138 g. of sodium), and methanol (5 cm3) was stirred at room temperature for 1 hour. Methyl cis-(2,5-dimethyl-2,5-dihydropyrrol-1-yl)acetate was then added (0.6 g.) and the mixture stirred overnight (16 h.). The solution was then evaporated and the residue partitioned between water (1.5 cm3) and ether (3 cm3). After stirring at 0° C. for about 3 hours a white precipitate separated. The precipitate was collected and washed with water and ether to give 0.24 g. of title base. The base was dissolved in isopropyl alcohol (3 cm3) and acidified with ethanolic hydrogen chloride. On cooling in ice the title compound hydrochloride was collected and washed with isopropyl alcohol. The product was then dissolved in hot ethanol (3 cm3) diluted with ethyl acetate (2 cm3) and cooled to give pure title compound as the hydrochloride (0.15 g.), m.p. 207°-9° C.

Workup

  1. stirringthe mixture stirred overnight (16 h.)
  2. customThe solution was then evaporated
  3. customthe residue partitioned between water (1.5 cm3) and ether (3 cm3)
  4. stirringAfter stirring at 0° C. for about 3 hours a white precipitate
  5. customseparated
  6. customThe precipitate was collected
  7. washwashed with water and ether
  8. customto give 0.24 g

Sources & evidence

ORD record
ord-a3325eee4c8048ff8cefb9aa226ae4cf
Source dataset
uspto-grants-1984_04
Patent number
US04443467

Reaction notes

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