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Sulfuric Acid → Z-D-Trp-Lys(BOC)-OMe

HRID 1435093
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1435093
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C1C=CC2N(O)N=NC=2C=1.[NH2:36][C@H:37]([C:50]([O:52][CH3:53])=[O:51])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].Cl.CN1CCOCC1.C(N=C=NC(C)C)(C)C.S(=O)(=O)(O)O>C1COCC1.O>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@@H:2]([C:13]([NH:36][C@H:37]([C:50]([O:52][CH3:53])=[O:51])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 1118Sulfuric AcidHCID 79724-MethylmorpholineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 700663N-(Benzyloxycarbonyl)-D-tryptophanHCID 16218818L-Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 57936723Z-D-Trp-Lys(BOC)-OMeAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 23.7 g Z-D-Trp-OH in 230 ml THF are added 9.5 g HOBt at RT. A clear colorless solution is formed. Then 20.8 g H-Lys(BOC)-OMe.HCl are added at RT, followed by 7.7 ml N-methylmorpholine. The fine suspension is cooled down to 0° and 11.4 ml diisopropylcarbodiimide added. Stirring 1 hour at 0°, then 3 hours at RT. A solution of 7.0 g sulfuric acid conc. in 120 ml water is added to the suspension. Extraction with 150 ml ethyl acetate, separation of the phases and washing of the organic phase consecutively with 100 ml brine saturated, 100 ml brine 25%, 5% sodium hydrogencarbonate solution. Then the organic phase is dried over MgSO4 and evaporated. The residue is taken up in 250 ml isopropyl acetate and stirred 2 hours at RT. Filtration and drying at 40° gives 40.9 g Z-D-Trp-Lys(BOC)-OMe, white substance. HPLC-conditions: MN Nucleosil 100 A/C 18; 5 micron; 250×4 mm; phase A: 0.24% phosphoric acid, phase B acetonitrile; gradient: from 20 to 80% B in 30 minutes; wavelength 220 nm; flow rate 1.3 ml/min; Temperature 35°: purity 97.8% b.a. (24.2 min).

Aufarbeitung

  1. customA clear colorless solution is formed
  2. temperatureThe fine suspension is cooled down to 0°
  3. custom3 hours
  4. customat RT
  5. extractionExtraction
  6. customwith 150 ml ethyl acetate, separation of the phases
  7. washwashing of the organic phase consecutively with 100 ml brine saturated, 100 ml brine 25%, 5% sodium hydrogencarbonate solution
  8. dry with materialThen the organic phase is dried over MgSO4
  9. customevaporated
  10. stirringstirred 2 hours at RT
  11. filtrationFiltration
  12. customdrying at 40°

Quellen und Nachweise

ORD-Eintrag
ord-44c5f7d2069f4f55ab6c04e07867bc4f
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07615609B2

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