Ammonium Chloride → 2,2-Bis(tert-butoxycarbonylamino)-5-(1-ethoxycarbonyl-ethylamino)-pentanoic acid benzyl ester

HRID 71751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71751
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].[CH2:15]([O:22][C:23](=[O:45])[C:24]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]CC=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[CH2:47]([O:49][C:50](=[O:54])[C@H:51]([CH3:53])[NH2:52])[CH3:48].[Cl-].[NH4+]>ClCCl>[CH2:15]([O:22][C:23](=[O:45])[C:24]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:31])([NH:37][C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:25][CH2:1][CH2:2][NH:52][CH:51]([C:50]([O:49][CH2:47][CH3:48])=[O:54])[CH3:53])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 866488762,2-Bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester

Produkt 1

HCID 866488772,2-Bis(tert-butoxycarbonylamino)-5-(1-ethoxycarbonyl-ethylamino)-pentanoic acid benzyl esterAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (5 g, 23.5 mmol) was added to a solution of 2,2-bis(tert-butoxycarbonylamino)-5-oxo-pentanoic acid benzyl ester (3.34 g, 7.9 mmol) and alanine ethyl ester hydrochloride (3.62 g, 23.5 mmol) in dichloromethane (30 mL). After 1 hour saturated ammonium chloride (10 mL) was added and the mixture was stirred for 5 minutes. The aqueous phase was extracted with dichloromethane (2×15 mL), and the combined organic phases were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The resulting residue was subjected to flash chromatography with eluent of (10% methanol in ethyl acetate) and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to provide 2,2-bis(tert-butoxycarbonylamino)-5-(1-ethoxycarbonyl-ethylamino)-pentanoic acid benzyl ester (1.7 g, 3.3 mmol, 41%). C27H42N2O8 calculated 522.3 observed [M+1]+ 523.3; rt=2.08 min.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with dichloromethane (2×15 mL)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-02e10797ba084f81b0e3d077ab2ccba2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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