Reaktion #595319

ord-8364dc09c1dc4d2d89d557ecc4b19c5d

Reaktionsgleichung

CC(C)(C)OC(=O)N[C@H](COS(C)(=O)=O)c1ccccc1
(S)-2-Phenyl-2-tert-butoxycarbonylaminoethyl methanesulfonate
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water
→
CC(C)(C)OC(=O)N[C@H](CN=[N+]=[N-])c1ccccc1
title compound
Ausbeute 76.0%
CC(C)(C)OC(=O)N[C@H](CN=[N+]=[N-])c1ccccc1
(S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide
Ausbeute 76.0%

Edukte

CC(C)(C)OC(=O)N[C@H](COS(C)(=O)=O)c1ccccc1
(S)-2-Phenyl-2-tert-butoxycarbonylaminoethyl methanesulfonate
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Temperatur
55°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled to room temperature
  2. 2
    workup.STIRRINGstirred vigorously for 20 minutes
  3. 3
    FiltrationPrecipitate was collected by filtration
  4. 4
    Waschenwashed with water
  5. 5
    Sonstigedried

Vorschrift

(S)-2-Phenyl-2-tert-butoxycarbonylaminoethyl methanesulfonate (15.77 g, 0.05 mol) was dissolved in 50 mL DMF followed by the addition of sodium azide (19.5 g, 0.3 mol). The mixture was stirred for 24 hrs at 55° C., cooled to room temperature, poured into cold water (500 mL) and stirred vigorously for 20 minutes. Precipitate was collected by filtration, washed with water and dried, affording 9.97 g of the title compound as a white solid. Yield: 76%; (MH)+=263; 1H NMR (DMSO-d6): 1.37 (s, 9H), 3.36-3.50 (m, 2H), 4.69-4.75 (m, 1H), 7.23-7.36 (m, 5H), 7.65-7.68 (d, J=9.2 Hz, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09095575B2uspto-grants-2015_08