2-Aminopyridine → N-[4-(2-pyridylamino-carbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester

HRID 1493450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1493450
[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:5][C:6](=[O:27])[C@H:7]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10](O)=[O:11].[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:37])[C@H:4]([CH2:28][S:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:5][C:6](=[O:27])[C@H:7]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:8][C@H:9]([C:10]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1)=[O:11])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 104392-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14997155N-[(S,S)-2,4-dibenzyl-4-carboxy-butyryl]-S-benzyl-(L)-cysteine methyl ester

Produkt 1

HCID 18645479N-[4-(2-pyridylamino-carbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2.1 g of N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-S-benzyl-(L)-cysteine methyl ester 0.60 g of 2-aminopyridine and 1.2 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 25 ml of methylene chloride is stirred at room temperature overnight. The mixture is concentrated, ethyl acetate is added and washed with water, sodium bicarbonate, dried (Na2SO4), filtered and concentrated. The residue is chromatographed on silica gel eluting with ethyl acetatemethylene chloride (1:9) to give N-[4-(2-pyridylaminocarbonyl)-(S,S)-2,4-dibenzylbutyryl]-S-benzyl-(L)-cysteine methyl ester (oil).

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. additionethyl acetate is added
  3. washwashed with water, sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel eluting with ethyl acetatemethylene chloride (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-5b016dc9251c4f8b8f66f367b1e8a11d
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021430

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