Triethylamine → HCID 178501061, compound

HRID 1893350Notes

Reaction equation

HRID 1893350 reaction equation
[C:1](=[N:4][OH:5])([NH2:3])[CH3:2].C(N(CC)CC)C.[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23](Cl)=O)[CH2:19][CH2:18]1)=[O:16]>O1CCCC1>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]2[O:5][N:4]=[C:1]([CH3:2])[N:3]=2)[CH2:19][CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 30926N-HydroxyacetamidineHCID 178501148HCID 178501148, compound

Product 1

HCID 178501061HCID 178501061, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetamide oxime (0.19 g, 2.6 mmol) and triethylamine (0.36 ml, 2.6 mmol) in tetrahydrofuran (24 ml) was added trans-4-chlorocarbonyl-cyclohexanecarboxylic acid methyl ester (0.50 g, 2.4 mmol) at 0-5° C. After completed addition the cooling bath was removed, and the mixture was stirred for 30 minutes. The precipitated ammonium salts were removed by filtration and washed with tetrahydrofuran. The filtrate was concentrated to dryness. The residue was redissolved in 1,4-dioxane (24 ml). The mixture was treated with a catalytic amount of toluene-4-sulfonic acid monohydrate and heated at reflux over night (16 h). The solvent was evaporated. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.48 g, 88%) as light brown oil. MS m/e: 225 ([M+H]+)

Workup

  1. additionaddition the cooling bath
  2. customwas removed
  3. customThe precipitated ammonium salts were removed by filtration
  4. washwashed with tetrahydrofuran
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was redissolved in 1,4-dioxane (24 ml)
  7. additionThe mixture was treated with a catalytic amount of toluene-4-sulfonic acid monohydrate
  8. temperatureheated
  9. temperatureat reflux over night (16 h)
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bb06ca2c1c6f4535954c842b5d027f2e
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

Loading…