Sodium Hydroxide → HCID 18628707, compound

HRID 1060735Notes

Reaction equation

HRID 1060735 reaction equation
[CH:1]1([CH2:7][CH:8]([C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])[C:9]([O:11]CC)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O.[Cl-].[Na+].O>[CH:1]1([CH2:7][CH:8]([C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:15])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 18628782HCID 18628782, compound

Product 1

HCID 18628707HCID 18628707, compoundYield 40.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution comprised of ethyl 2-cyclohexylmethyl-N-phenethylmalonamate (366 mg, 1.106 mmol) in ethanol (10 mL) was treated with 1N aqueous sodium hydroxide (1.3 mL) for 2.5 hours and then diluted with water (30 mL) and brine (10 mL). The dilution was extracted with diethyl ether (3×30 mL). The aqueous layer was cooled to 0° C., acidified with 1N hydrochloric acid (2 mL) and extracted with ethyl acetate (3×30 mL). The combined ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated to provide 2-cyclohexylmethyl-N-phenethyhnalonamic acid (138 mg, 0.45 mmol).

Workup

  1. extractionThe dilution was extracted with diethyl ether (3×30 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1664a82a6dc74e87b84d5a52a3765f91
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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