Triethylamine → 1-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide

HRID 65721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65721
[CH3:1][O:2][C:3]([CH2:5][CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11](O)=[O:12])=[O:8])=[O:4].C(OC(Cl)=O)C(C)C.C([N:28](CC)CC)C>ClCCl>[CH3:1][O:2][C:3]([CH2:5][CH:6]([CH3:17])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([NH2:28])=[O:12])=[O:8])=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 538488431-(3-Methoxycarbonyl-2-methylpropanoyl)-L-proline

Produkt 1

HCID 227996501-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(3-Methoxycarbonyl-2-methylpropanoyl)-L-proline (2.4 g.) is dissolved in a mixture of dichloromethane (50 ml.) and triethylamine (1.4 ml.). The solution is chilled in an ice water bath and isobutylchloroformate (1.36 g.) is added while the mixture is stirred. After 10 minutes ammonia (gas) is bubbled through the solution, still in the ice bath, for 15 minutes. The reaction mixture is stirred for 1 hour at room temperature, diluted with methylene chloride (100 ml.) and washed with water, 0.1 N hydrochloric acid, water, and dried over magnesium sulfate. The solvent is removed in vacuo to yield 1-(3-methoxycarbonyl-2-methylpropanoyl)-L-prolineamide.

Aufarbeitung

  1. temperatureThe solution is chilled in an ice water bath
  2. customAfter 10 minutes ammonia (gas) is bubbled through the solution, still in the ice bath, for 15 minutes
  3. stirringThe reaction mixture is stirred for 1 hour at room temperature
  4. additiondiluted with methylene chloride (100 ml.)
  5. washwashed with water, 0.1 N hydrochloric acid, water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-40c01b10911e4e469b1041feeec04028
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04128653

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