Hydrochloric Acid → HCID 14025168, compound

HRID 1722628Notes

Reaction equation

HRID 1722628 reaction equation
C[O:2][CH:3](OC)[C:4]1[NH:5][C:6]([CH3:30])=[C:7]([P:23]2(=[O:29])[O:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[CH:3]([C:4]1[NH:5][C:6]([CH3:30])=[C:7]([P:23]2(=[O:29])[O:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14025165HCID 14025165, compound

Product 1

HCID 14025168HCID 14025168, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dimethylacetal (3.04 g) obtained in Example 1 was dissolved in 30 ml of acetone, 2 ml of 6N hydrochloric acid was dropped therein with ice cooling and stirring, and the mixture was kept at 5° C. in a refrigerator for 4 days. To the reaction solution was added 30 ml of ice water, the mixture was neutralized with sodium bicarbonate, concentrated in vacuo at room temperature, the residual solution was extracted with chloroform, the chloroform layer was washed with sodium chloride solution, evaporated to dryness, the residue was purified by subjecting to a flash column chromatography, and the 1.38 g of resulting crude crystals were recrystallized from etherethyl acetate to give yellow prisms. M.p. 135°-136° C.

Workup

  1. concentrationconcentrated in vacuo at room temperature
  2. extractionthe residual solution was extracted with chloroform
  3. washthe chloroform layer was washed with sodium chloride solution
  4. customevaporated to dryness
  5. customthe residue was purified
  6. customthe 1.38 g of resulting crude crystals
  7. customwere recrystallized from etherethyl acetate
  8. customto give yellow prisms

Sources & evidence

ORD record
ord-ffd077364424460fbeb04b3a8aff41bd
Source dataset
uspto-grants-1989_08
Patent number
US04857515

Reaction notes

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