4-Methylmorpholine → Z-Asp(OtBu)-Leu-OBzl

HRID 1417140

Reaktionsgleichung

Reaktionsgleichung von HRID 1417140
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:39][C@H:40]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:41][CH:42]([CH3:44])[CH3:43]>C1COCC1.C(N(CC)CC)C>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([NH:39][C@H:40]([C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])[CH2:41][CH:42]([CH3:44])[CH3:43])=[O:13])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 6451313Benzyl L-leucinate

Produkt 1

HCID 131721133Z-Asp(OtBu)-Leu-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Z-Asp(OtBu)-OH (10.23 g) in THF (50 mL) was added N-methyl-morpholine (3.30 mL) and isobutyl chloroformate (3.90 mL) at -20° C. After 10 min, the reaction mixture was added to the solution of H-Leu-OBzl (11.81 g in 50 mL HCl3) at -20° C., followed by addition of triethylamine (4.18 mL). The resulting mixture was allowed to warm to room temp. After filtering off the salt, the filtrate was concentrated to an oil. The oil was dissolved in 100 mL of ethyl acetate; washed with 0.2N HCl, 5% NaHCO3 and sat. NaCl; dried over Na2SO4. After filtration, the solvent was evaporated to give Z-Asp(OtBu)-Leu-OBzl as an oil of 14.81 g.

Aufarbeitung

  1. filtrationAfter filtering off the salt
  2. concentrationthe filtrate was concentrated to an oil
  3. dissolutionThe oil was dissolved in 100 mL of ethyl acetate
  4. washwashed with 0.2N HCl, 5% NaHCO3 and sat. NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ead94c459d5c470abb0a857f00ba5182
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05876945

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