Hydrazine hydrate (1:1) → (S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 339273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339273
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:22][NH2:23]>CO>[NH:22]([C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:23]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 9882138Boc-L-phenylalanine methyl ester

Produkt 1

HCID 6710869(S)-tert-Butyl (1-hydrazinyl-1-oxo-3-phenylpropan-2-yl)carbamateAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate (Aldrich, 300 mg, 1.07 mmol) in MeOH (5.4 mL) was added hydrazine hydrate (170 μL, 3.44 mmol). The resulting solution was stirred at room temperature overnight and then concentrated in vacuo. The residue was triturated with hexanes (2×) and then from a minimal amount of 2:3 hexanes/MeOH (2×) to give the title compound (195 mg, 65%) as a white solid. 1H NMR (CDCl3) δ 7.41-7.25 (m, 3H), 7.20 (d, J=6.8 Hz, 2H), 4.39-4.21 (m, 1H), 3.07 (d, J=7.0 Hz, 2H), 1.42 (s, 9H); MS (ESI+) m/z 280.3 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with hexanes (2×)

Quellen und Nachweise

ORD-Eintrag
ord-8deb19f9a01541dea5cbd3f514200779
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889712B2

Notizen zur Reaktion

Wird geladen…