Acetic Acid → N-(2-Cyclohexyl-3-hydroxypropyl) glycine, methyl ester

HRID 2108183Notes

Reaction equation

HRID 2108183 reaction equation
[NH2:1][CH2:2][CH:3]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:4][OH:5].[CH3:12][O:13][CH:14]([OH:19])[C:15](OC)=O.C(O)(=O)C>CO.[Pd]>[CH:6]1([CH:3]([CH2:4][OH:5])[CH2:2][NH:1][CH2:15][C:14]([O:13][CH3:12])=[O:19])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724791Methyl 2-Hydroxy-2-methoxyacetateHCID 150564193-Amino-2-cyclohexylpropan-1-ol

Product 1

HCID 15056420N-(2-Cyclohexyl-3-hydroxypropyl) glycine, methyl esterYield 53.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 3-amino-2-cyclohexyl-1-propanol (1 g, 6.37 mmole) and methyl glyoxylate methylhemiacetal (790 mg, 6.56 mmole; see Tetrahedron, 881, 1977) in methanol (9 ml) was stirred at room temperature under argon for 24 hours. The resulting solution was transferred to a Parr bottle, treated with additional methanol (22 ml), acetic acid (3.6 ml), and 10% Pd on carbon (857 mg) and hydrogenated at 50 psi overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo. Acetic acid was removed by evaporation from toluene. The residue was partitioned between ethyl acetate and 1N HCl. The organic layer was extracted with additional HCl and the combined aqueous extracts were washed with ethyl acetate. The pH of the product rich aqueous solution was raised to 10.2, and sodium chloride was added to saturation. Extraction with ethyl acetate followed by drying (sodium sulfate), filtration and concentration in vacuo produced 780 mg (53%) of the title compound as an oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customAcetic acid was removed by evaporation from toluene
  4. customThe residue was partitioned between ethyl acetate and 1N HCl
  5. extractionThe organic layer was extracted with additional HCl
  6. washthe combined aqueous extracts were washed with ethyl acetate
  7. temperatureThe pH of the product rich aqueous solution was raised to 10.2, and sodium chloride
  8. additionwas added to saturation
  9. extractionExtraction with ethyl acetate
  10. customby drying
  11. filtration(sodium sulfate), filtration and concentration in vacuo

Sources & evidence

ORD record
ord-c0652365f3134c74ad15c72c00e9ad1f
Source dataset
uspto-grants-1990_06
Patent number
US04937355

Reaction notes

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