L-Aspartic Acid → 4-tert-Butyl hydrogen L-aspartate

HRID 857826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857826
N[C@H](C(O)=O)CC(=O)O.[NH:10](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>ClCCl.N1CCCCC1>[NH2:10][C@H:11]([C:20]([OH:22])=[O:21])[CH2:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17]

Komponenten

4

Edukt 2

HCID 5960L-Aspartic AcidHCID 2724635Fmoc-L-Asp(OtBu)-OH

Produkt 1

HCID 70105704-tert-Butyl hydrogen L-aspartateAusbeute 110,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67144590Dichloromethane piperidineLösungsmittel

Versuchsvorschrift

Synthesis of Asp(OtBuj-OH. Fmoc-Asp(OtBu)-OH (500 mg, 1.2 mmole) was dissolved in a 9:1 mixture of dichloromethane-piperidine (5 mL) in a 25 mL round-bottomed flask. The reaction mixture was stirred overnight at room temperature. The next morning, TLC analysis indicated complete Fmoc deprotection. The reaction mixture was concentrated by rotoevaporation, coevaporated 2 times with toluene, and dried under vacuum to give a crude oil. This oil was purified by flash chromatography on silica gel (50 g) using a stepwise solvent gradient of 10%–50% methanol in dichloromethane to afford 250 mg (100%) of Asp(OtBu)-OH.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated by rotoevaporation
  2. customdried under vacuum
  3. customto give a crude oil
  4. customThis oil was purified by flash chromatography on silica gel (50 g)

Quellen und Nachweise

ORD-Eintrag
ord-69e5d20e92f14e0aa90662250c458fb2
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148030B2

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