Hydrochloric Acid → HCID 15231784, compound

HRID 274943Notes

Reaction equation

HRID 274943 reaction equation
[C:1]([CH:6]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17](C(OCC)=O)[C:16]2=[O:29])=[CH:10][C:9]=1[CH2:30][CH3:31])([O:3]CC)=[O:2].C(O)C.[OH-].[Na+].Cl>C(Cl)Cl>[C:1]([CH:6]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:29])=[CH:10][C:9]=1[CH2:30][CH3:31])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 20089207HCID 20089207, compound

Product 1

HCID 15231784HCID 15231784, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with 0.031 g (0.06 mmol) of the product of step C, 0.5 mL of ethanol and the flask and its contents were placed in a sonicator bath. Methylene chloride (0.2 mL) was then added in order to completely dissolve the starting material. Next, 23 μL of a 5.0 N solution of sodium hydroxide were added and the reaction was stirred at room temperature overnight. The reaction mixture was then adjusted to pH=5 with dropwise addition of 6 N hydrochloric acid, and then concentrated in vacuo. The residue was redissolved in methanol, filtered, and evaporated. The mixture was then purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH-NH4OH (80: 15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.012 g (48%) of the title compound.

Workup

  1. customthe flask and its contents were placed in a sonicator bath
  2. dissolutionto completely dissolve the starting material
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was redissolved in methanol
  5. filtrationfiltered
  6. customevaporated
  7. customThe mixture was then purified on a silica gel flash chromatography column
  8. washeluted with CHCl3 -MeOH-NH4OH (80: 15:1)
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-ee71c190056e4b4d9de502e373109ec5
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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