Hydrochloric Acid → HCID 54565707, compound

HRID 369544Notes

Reaction equation

HRID 369544 reaction equation
[OH-:1].[Na+].[CH3:3][C@H:4]([O:11][C:12]1[C:17]([NH:18]C(=O)C)=[CH:16][C:15](C2C=CC=CC=2C([O-])=O)=[C:14]([N+:31]([O-:33])=[O:32])[CH:13]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O.Cl>C(O)C>[CH3:3][C@H:4]([O:11][C:12]1[C:17]([NH2:18])=[CH:16][C:15]([OH:1])=[C:14]([N+:31]([O-:33])=[O:32])[CH:13]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 20588796HCID 20588796, compound

Product 1

HCID 54565707HCID 54565707, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydroxide (687 mg, 17.2 mmol) was carefully added to a stirred solution of 50a (294 mg, 0.69 mmol), water (8 ml), and ethanol (25 ml). The reaction mixture was stirred overnight at 25° C. and then was neutralized with concentrated HCl. The resulting solution was extracted twice with dichloromethane, and the combined organic layers were washed with brine and dried over MgSO4. The crude product was concentrated and purified via flash chromatography over silica gel with gradual elutions from 90/10 to 80/20 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 164 mg (84%) of an orange oil which eventually solidified.

Workup

  1. extractionThe resulting solution was extracted twice with dichloromethane
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationThe crude product was concentrated
  5. custompurified via flash chromatography over silica gel with gradual elutions from 90/10 to 80/20 (v/v, Hex/EtOAc)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-093bd4c5b3b64ebf90675a6a7d10c0ec
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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