Hydrochloric Acid → HCID 54040210, compound

HRID 369531Notes

Reaction equation

HRID 369531 reaction equation
[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](C2C=CC=CC=2C([O-])=O)=[CH:12][C:11]=1[N+:25]([O-:27])=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH2:28].O.[OH-].[Li+].Cl>CO>[CH3:1][C@H:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:28])=[CH:12][C:11]=1[N+:25]([O-:27])=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86755961HCID 86755961, compound

Product 1

HCID 54040210HCID 54040210, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Compound 32a (380 mg, 1.02 mmol) was dissolved in 10 ml methanol, and water (approximately 3 ml) was added until the solution remained milky yellow with vigorous stirring. Lithium hydroxide monohydrate (258 mg, 6.1 mmol) was added, the reaction mixture was stirred for six hours at 25° C., and then was acidified with concentrated HCl. The reaction mixture was extracted with dichloromethane (30 ml). The organic layer was separated, washed with saturated sodium bicarbonate, followed by brine, and dried over magnesium sulfate. The solvent was evaporated and the crude product was purified via flash chromatography over silica gel (50/50, v/v, Hex/EtOAc) to yield 269 mg (98%) of an orange oil.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (30 ml)
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified via flash chromatography over silica gel (50/50

Sources & evidence

ORD record
ord-7313d1cd4b0e400d9a37643fb59a3255
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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