N,N-Dimethyl-1,3-propanediamine → Benzyloxycarbonyl-isoleucyl-proline proline

HRID 1282958

Reaktionsgleichung

Reaktionsgleichung von HRID 1282958
Br.N1CCC[C@H]1C([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=O.[N+](C1C=CC([O:26][C:27](=[O:44])[C@H:28]([C@H:40]([CH2:42][CH3:43])[CH3:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=CC=1)([O-])=O.ON1C2C=CC=CC=2N=N1.CN(CCCN)C>CN(C)C=O.C(N(CC)CC)C>[CH2:33]([O:32][C:30]([NH:29][C@H:28]([C:27]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:44])[C@H:40]([CH2:42][CH3:43])[CH3:41])=[O:31])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[NH:29]1[CH2:43][CH2:42][CH2:40][C@H:28]1[C:27]([OH:26])=[O:44]

Komponenten

7

Edukt 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 757711-HydroxybenzotriazoleHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 68145334Prolyl-proline hydrobromide

Produkt 1

HCID 68146244Benzyloxycarbonyl-isoleucyl-proline prolineAusbeute 240,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Prolyl-proline hydrobromide (4.24 g) is dissolved in a mixture of dimethylformamide (40 ml) and triethylamine (2.8 ml). Benzyloxycarbonyl-isoleucine p-nitrophenyl ester (9.27 g) and 1-hydroxybenzotriazole (3 g) are added and the mixture is stored at room temperature for 16 hours. Dimethylaminopropylamine (1 ml) is added and after 2 hours the solvent is removed in vacuo. The residue is dissolved in ethyl acetate (200 ml) and washed sequentially with 0.1 N hydrochloric acid, and water. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to yield 13.8 g solid. This material is applied to a silica gel column (300 g) in ethyl acetate and eluted with the same solvent. The fractions containing the desired above-titled tripeptide are pooled and concentrated to dryness.

Aufarbeitung

  1. customis removed in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate (200 ml)
  3. washwashed sequentially with 0.1 N hydrochloric acid, and water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f539f9468b14564a0c78dd7fc405e85
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03973006

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