Phenol → (S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl ester

HRID 1026098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026098
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6][OH:7].[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][CH2:6][O:7][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10561607Methyl N-(tert-butoxycarbonyl)-L-homoserinate

Produkt 1

HCID 67178164(S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl esterAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (S)-(tert-butoxycarbonylamino)-4-hydroxybutyric acid methyl ester (1.43 g; CAS 120042-11-7) in THF (4 ml) were added phenol (692 mg), triphenylphosphine (1.77 g) and diisopropyl azodicarboxylate (1.36 g). The resulting yellow solution was stirred at room temperature overnight. The reaction mixture was evaporated and purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->90:10) to give (S)-2-tert-butoxycarbonylamino-4-phenoxy-butyric acid methyl ester (1.16 g, 61%) as a light yellow oil. MS (ISP): 210.1 ([M+H-BOC]+)).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. custompurified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->90:10)

Quellen und Nachweise

ORD-Eintrag
ord-8306639361e643ee84af9a633edb0cc2
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729113B2

Notizen zur Reaktion

Wird geladen…