Réaction #595319

ord-8364dc09c1dc4d2d89d557ecc4b19c5d

Équation de réaction

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
Rendement 76.0%
CC(C)(C)OC(=O)N[C@H](CN=[N+]=[N-])c1ccccc1
(S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide
Rendement 76.0%

Réactifs

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

Réactifs

Aucun

Solvants

CN(C)C=O
DMF

Conditions de réaction

Température
55°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurecooled to room temperature
  2. 2
    workup.STIRRINGstirred vigorously for 20 minutes
  3. 3
    FiltrationPrecipitate was collected by filtration
  4. 4
    Lavagewashed with water
  5. 5
    Autredried

Mode opératoire

(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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09095575B2uspto-grants-2015_08