Hydrochloric Acid → HCID 20149481, compound

HRID 568974Notes

Reaction equation

HRID 568974 reaction equation
[NH2:1][C:2]([C:16]([O:18]CC)=[O:17])([CH2:8][CH2:9][CH:10]([F:15])[CH:11]([NH2:14])[CH:12]=[CH2:13])[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl.C1OC1C>C(O)C.C(O)(C)C>[NH2:1][C:2]([C:16]([OH:18])=[O:17])([CH2:8][CH2:9][CH:10]([F:15])[CH:11]([NH2:14])[CH:12]=[CH2:13])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6378Propylene OxideHCID 14798Sodium HydroxideHCID 20149487HCID 20149487, compound

Product 1

HCID 20149481HCID 20149481, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

The crude material 23 (11.5 g, about 31 mmoles since some solvent left) is dissolved in ethanol (150 mL) and 2N NaOH (150 mL) and stirred at room temperature for 3 hours. The mixture is neutralized with conc. HCl (about 25 mL) with cooling, then acidified (HCl). After evaporation and drying, the residue is dissolved in ethanol, filtered through millipore, and evaporated again. Dissolving in water, filtration, and evaporation yields a solid (11 g, 2 g more than theory). This is dissolved in isopropanol (130 mL) and treated with propylene oxide (6.5 mL, 3 equivalents). Crude 24 (7.2 g, somewhat more than theory) is collected. Thin layer chromatography (ethanol/NH4OH 80/20 revelation ninhydrin) indicates the presence of some decarboxylated product. The compound 24 is used without further purification. Recrystallization from water/ethanol is possible. Caution: no heating!

Workup

  1. temperaturewith cooling
  2. customAfter evaporation
  3. customdrying
  4. dissolutionthe residue is dissolved in ethanol
  5. filtrationfiltered through millipore
  6. customevaporated again
  7. dissolutionDissolving in water
  8. filtrationfiltration, and evaporation
  9. customyields a solid (11 g, 2 g more than theory)
  10. customCrude 24 (7.2 g, somewhat more than theory) is collected
  11. customThe compound 24 is used without further purification
  12. customRecrystallization from water/ethanol

Sources & evidence

ORD record
ord-409d3eeb86f647a9beb79440f12b5c41
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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