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Hydrochloric Acid → H-Leu-Leu-Lys(Z)-OBzl

HRID 849693
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 849693
Cl.[NH:2](C(OC(C)(C)C)=O)[C@H:3]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].COC(C)(C)C>C(OCC)(=O)C>[NH2:2][C@H:3]([C:8]([NH:10][C@H:11]([C:16]([NH:18][C@H:19]([C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 12020549Boc-Leu-Leu-Lys(Z)-OBzl

Produkt 1

HCID 12020550H-Leu-Leu-Lys(Z)-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-12.5 °C

Versuchsvorschrift

A cooled solution (-15° C.) of gaseous HCl (50.0 g, 1.37 mol) in ethyl acetate (250 g) was added to Boc-Leu-Leu-Lys(Z)-OBzl (50.0 g, 71.7 mmol) at -15 to -10° C. over 15 min. The mixture was stirred at -15 to -10° C. for 75 min and t-butyl methyl ether (310 g) was added over 25 min. The temperature was allowed to rise to about -8 to -5° C. and the excess HCl was removed under reduced pressure. Another portion of t-butyl methyl ether (310.0 g) was added over 15 min and the reaction temperature was maintained at -5° C. for approximately 2 h. The resulting solid product, H-Leu-Leu-Lys(Z)-OBzl·HCl was filtered and rinsed with t-butyl methyl ether then dried to give 41.8 g, 92.1%.

Aufarbeitung

  1. customto rise to about -8 to -5° C.
  2. customthe excess HCl was removed under reduced pressure
  3. additionAnother portion of t-butyl methyl ether (310.0 g) was added over 15 min
  4. temperaturethe reaction temperature was maintained at -5° C. for approximately 2 h
  5. filtrationThe resulting solid product, H-Leu-Leu-Lys(Z)-OBzl·HCl was filtered
  6. washrinsed with t-butyl methyl ether
  7. customthen dried
  8. customto give 41.8 g, 92.1%

Quellen und Nachweise

ORD-Eintrag
ord-6649136021f8429a81cdbf3ca9cf4a44
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06013764

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