Dicyclohexylcarbodiimide → palmitoyl-L-Ala-D-Glu(OSu)OBzl

HRID 4423

Reaktionsgleichung

Reaktionsgleichung von HRID 4423
[NH:1]([C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:24])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].O[N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(Cl)(Cl)Cl>[NH:1]([C:23]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:24])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:11])[O:12][N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47])=[O:5])[CH3:3]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 131714154palmitoyl-L-Ala-D-Glu(OH)OBzl

Produkt 1

HCID 131714153palmitoyl-L-Ala-D-Glu(OSu)OBzlAusbeute 7.846,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1)(1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with chloroform. The filtrate was concentrated in vacuo and the diisopropylether was added to the residue. The product was collected and dried to afford palmitoyl-L-Ala-D-Glu(OSu)OBzl (2)(170 g).

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe diisopropylether was added to the residue
  5. customThe product was collected
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-34b5a02bca8a409287c4f086e8e5d348
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725582

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