1,2-Dichloroethane → Benzyl((4S)-4-[(tert-butoxycarbonyl)amino]-5-{[(1S)-3-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)propyl]amino}-5-oxopentyl)carbamate

HRID 269620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269620
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:24]([OH:26])=O)[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:28][C@H:29]([CH2:40][OH:41])[CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:24]([NH:28][C@H:29]([CH2:40][OH:41])[CH2:30][CH2:31][NH:32][C:33]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:39])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 57463635tert-Butyl [(3S)-3-amino-4-hydroxybutyl]carbamate hydrochloride

Produkt 1

HCID 131727148Benzyl((4S)-4-[(tert-butoxycarbonyl)amino]-5-{[(1S)-3-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)propyl]amino}-5-oxopentyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Preparation takes place in analogy to Example 79A from 140 mg (0.38 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine and 120 mg (0.50 mmol) of tert-butyl [(3S)-3-amino-4-hydroxybutyl]carbamate hydrochloride (Example 88A) in 6 ml of dimethylformamide with the addition of 96 mg (0.50 mmol) of EDC, 16 mg (0.12 mmol) of HOBt and 0.17 ml (1.00 mmol) of diisopropylethylamine. The product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→10:90).

Aufarbeitung

  1. customPreparation
  2. customThe product is purified by preparative RP-HPLC (mobile phase water/acetonitrile gradient: 90:10→10:90)

Quellen und Nachweise

ORD-Eintrag
ord-d87cf6018eae4e56837cff4462dc92be
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446102B2

Notizen zur Reaktion

Wird geladen…