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

HRID 2226592

Reaktionsgleichung

Reaktionsgleichung von HRID 2226592
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e2fb56f4209249dc8ea1639dfb0967c6
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05348955

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