Methanol → (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

HRID 451867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451867
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C.CO>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 7018756(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid

Produkt 1

HCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution (S)-2-(tert-butoxycarbonylamino)-5-methoxy-5-oxopentanoic acid (26.1 g, 0.1 mol) in THF (500 mL), BH3.Me2S (80 mL, 0.8 mmol) was added dropwise at −78° C., then stirred at rt for 3 hrs. The reaction was stopped by careful addition of methanol. After evaporation and three distillations of methanol, the residue was dissolved in EtOAc, washed with 1 M NaHCO3, and brine. (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate (12 g, yield 49%) was obtained as an oil that was used in the next step without further purification.

Aufarbeitung

  1. customAfter evaporation and three distillations of methanol
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with 1 M NaHCO3, and brine

Quellen und Nachweise

ORD-Eintrag
ord-7c10b6e8df794ab78bcc16b9d584b0d9
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

Notizen zur Reaktion

Wird geladen…