Triethylamine → 4-Dipentylcarbamoyl-1-(2,2-diphenylacetyl)hexahydro-2-pyrazinecarboxylic acid

HRID 486744

Reaction equation

HRID 486744 reaction equation
[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]2[C:16]([OH:18])=[O:17])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:32]([N:37]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:38](Cl)=[O:39])[CH2:33][CH2:34][CH2:35][CH3:36]>C1COCC1>[CH2:41]([N:37]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:38]([N:13]1[CH2:14][CH2:15][N:10]([C:8](=[O:9])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:11]([C:16]([OH:18])=[O:17])[CH2:12]1)=[O:39])[CH2:42][CH2:43][CH2:44][CH3:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18965159(+/-)-1-(Diphenylacetyl)-2-piperazinecarboxylic acidHCID 22106956Dipentylcarbamyl chloride

Product 1

HCID 189651744-Dipentylcarbamoyl-1-(2,2-diphenylacetyl)hexahydro-2-pyrazinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 79 mg (0.24 mmole) of (±)-1-(diphenylacetyl)piperazine-2-carboxylic acid (from Example 2, Step A) and 2 ml of THF was treated with 49 mg (0.48 mmole) of triethylamine to give a solution which was cooled to 0° C. With stirring a solution of 61 mg (0.25 mmole) of dipentylcarbamoyl chloride (from Step A) in 0.5 ml of THF was added and the solution was briefly warmed to 50° C. and then stirred at 25° C. for 16 hours. The resulting mixture was filtered and the filtrate was concentrated in vacuo to an oil which was dissolved in 0.5 ml of methanol and was chromatographed over an 85×0.9 cm. LH-20 column with 1.7 ml fractions of methanol. Fractions 21-25 were combined and concentrated in vacuo to 70 mg (57%) of oil.

Workup

  1. customto give a solution which
  2. additionwas added
  3. temperaturethe solution was briefly warmed to 50° C.
  4. filtrationThe resulting mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo to an oil which
  6. dissolutionwas dissolved in 0.5 ml of methanol
  7. customwas chromatographed over an 85×0.9 cm
  8. concentrationconcentrated in vacuo to 70 mg (57%) of oil

Sources & evidence

ORD record
ord-207c70ec8c2b433ba3bbb1860dc59567
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Linked notes

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