Triethylamine → HCID 178516175, Verbindung

HRID 1606823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606823
[CH2:1]([O:8][C:9](=[O:27])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[C:32](=[O:33])[CH2:31][CH2:30][C@H:29]1[C:34]([NH:36][C@H:37]([C:44]([NH:46][C@H:47]([C:58]([NH:60][C@H:61]([C:64](O)=[O:65])[CH2:62][OH:63])=[O:59])[CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)=[O:45])[CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1)=[O:35].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:27])[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)[NH:11][C:62](=[O:63])[C@H:61]([CH2:64][OH:65])[NH:60][C:58](=[O:59])[C@H:47]([CH2:48][C:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[NH:51][CH:50]=1)[NH:46][C:44](=[O:45])[C@H:37]([CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1)[NH:36][C:34](=[O:35])[C@@H:29]1[CH2:30][CH2:31][C:32](=[O:33])[NH:28]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 7408223(S)-Benzyl 2-amino-3-(4-(benzyloxy)phenyl)propanoateHCID 178516176HCID 178516176, Verbindung

Produkt 1

HCID 178516175HCID 178516175, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

O-Benzyl-L-tyrosine benzyl ester (VIII) hydrochloride (0.397 g) and L-pyroglutamyl-L-histidyl-L-tryptophyl-L-serine (VII) (0.539 g) in dry dimethylformamide (50 ml) is treated with triethylamine (0.14 ml) and dicyclohexylcarbodiimide (0.227 g) in dry dimethylformamdie (5 ml) at 0° C. After stirring at room temperature for 24 hours, the reaction mixture is evaporated to dryness. The residue is triturated in methanol and the dicyclohexylurea is removed by filtration. The filtrate is concentrated to L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-O-benzyl-L-tyrosine benzyl ester (IX).

Aufarbeitung

  1. customthe reaction mixture is evaporated to dryness
  2. customThe residue is triturated in methanol
  3. customthe dicyclohexylurea is removed by filtration
  4. concentrationThe filtrate is concentrated to L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-O-benzyl-L-tyrosine benzyl ester (IX)

Quellen und Nachweise

ORD-Eintrag
ord-f6dcd921fdad48aaa24898bdb968449f
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953416

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