Hydrochloric Acid → HCID 67078544, compound

HRID 1475644Notes

Reaction equation

HRID 1475644 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=1)([O-:5])=[O:4].O.Cl>C1COCC1.CO>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:13]([OH:15])=[O:14])=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68170290HCID 68170290, compound

Product 1

HCID 67078544HCID 67078544, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.03 g (25.8 mmol) of sodium hydroxide were added to a solution of 715 mg (2.6 mmol) of (+/−)-ethyl (4-nitrophenyl)(cyclopentyl)acetate in 6 ml of THF/methanol (1:1), and the mixture was stirred at RT overnight. The reaction mixture was then poured into water, neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated. The residue was taken up in 80 ml of diethyl ether, and 250 ml of petroleum ether were added. The precipitated solid was filtered off with suction and washed with petroleum ether. The product obtained in this manner was purified further by preparative HPLC. This gave 89.5 mg (14% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated
  4. addition250 ml of petroleum ether were added
  5. filtrationThe precipitated solid was filtered off with suction
  6. washwashed with petroleum ether
  7. customThe product obtained in this manner
  8. customwas purified further by preparative HPLC

Sources & evidence

ORD record
ord-319c9b91aede43e5b1ed153e55f8f07b
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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