Hydrochloric Acid → HCID 18521101, compound

HRID 413642Notes

Reaction equation

HRID 413642 reaction equation
[OH-:1].[Na+].[CH2:3]([O:10][C:11]1[C:16]([NH:17]C(=O)C)=[CH:15][C:14](C2C=CC=CC=2C([O-])=O)=[C:13]([N+:30]([O-:32])=[O:31])[CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].Cl>C(O)C.O>[CH2:3]([O:10][C:11]1[C:16]([NH2:17])=[CH:15][C:14]([OH:1])=[C:13]([N+:30]([O-:32])=[O:31])[CH:12]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18521027HCID 18521027, compound

Product 1

HCID 18521101HCID 18521101, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (2.15 g, 53.7mmol) was carefully added to a stirred solution of 50b (890 mg, 2.15 mmol) in 80 ml ethanol and 20 ml water. The reaction mixture was stirred overnight and was then acidified with concentrated HCl. Extracted three times with dichloromethane, and the combined organic layers were washed with brine and dried over MgSO4. The crude product was adsorbed onto silica gel and purified via flash chromatography with gradual elutions from 85/10/5 to 75/20/5 (Hex/EtOAc/dichloromethane). Evaporation of solvent yielded 469 mg (81%) of an orange solid.

Workup

  1. extractionExtracted three times with dichloromethane
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. custompurified via flash chromatography with gradual elutions from 85/10/5 to 75/20/5 (Hex/EtOAc/dichloromethane)
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-1655ae7fc9764202b3ea6136b8573b03
Source dataset
uspto-grants-2003_05
Patent number
US06569504B1

Reaction notes

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