Dicyclohexylcarbodiimide → Z-Sta-Ile-His-Lys(Boc)-OMe

HRID 1982310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982310
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([OH:12])=O)[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:23][C@H:24]([C:29]([NH:31][C@H:32]([C:39]([NH:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)=[O:30])[C@H:25]([CH2:27][CH3:28])[CH3:26].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C@H:7]([CH2:9][C:10]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:39]([NH:41][C@H:42]([C:55]([O:57][CH3:58])=[O:56])[CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:48]([O:50][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:49])=[O:40])[CH2:33][C:34]1[N:38]=[CH:37][NH:36][CH:35]=1)=[O:30])[C@H:25]([CH2:27][CH3:28])[CH3:26])=[O:12])[OH:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14560231Z-Sta-OHHCID 178455961HCID 178455961, Verbindung

Produkt 1

HCID 178455902Z-Sta-Ile-His-Lys(Boc)-OMe

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

900 mg of Z-Sta-OH (for manufacture see stage 1.12), 1.24 g of H-Ile-His-Lys(Boc)-OMe and 560 mg of HOBt×H2O are dissolved in 13 ml of DMF. After the addition of 600 mg of DCCI, the whole is left to stand at room temperature for 20 hours, then the DCH which has crystallised out is filtered off and the filtrate is concentrated to dryness. The greasy residue is triturated at 0° with 30 ml of diisopropyl ether, the solvent is decanted and the residue is dried. Purification is carried out by Craig partitioning in the system methanol/buffer/ethylene chloride/chloroform (10:3:8:4; buffer=14.3 ml of glacial acetic acid and 9.6 g of ammonium acetate in 1000 ml of H2O) over 700 stages. The thin layer chromatographically pure fractions (K=0.5) are combined, strongly concentrated and lyophilised. To remove acetic acid, the product is dissolved and reprecipitated from 5% strength methanolic NaHCO3 solution, yielding Z-Sta-Ile-His-Lys(Boc)-OMe in the form of amorphous powder; Rf (B)=0.8; Rf (I)=0.56.

Aufarbeitung

  1. waitthe whole is left
  2. customthe DCH which has crystallised out
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness
  5. customThe greasy residue is triturated at 0° with 30 ml of diisopropyl ether
  6. customthe solvent is decanted
  7. customthe residue is dried
  8. customPurification
  9. custompartitioning in the system methanol/buffer/ethylene chloride/chloroform (10:3:8:4; buffer=14.3 ml of glacial acetic acid and 9.6 g of ammonium acetate in 1000 ml of H2O) over 700 stages
  10. concentrationstrongly concentrated
  11. customTo remove acetic acid
  12. dissolutionthe product is dissolved
  13. customreprecipitated from 5% strength methanolic NaHCO3 solution

Quellen und Nachweise

ORD-Eintrag
ord-e32981ec52c04655b8b1c9f76a43e0db
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04595677

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