Reaction #595319

ord-8364dc09c1dc4d2d89d557ecc4b19c5d

Reaction equation

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

Reactants

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

Reagents

None

Solvents

CN(C)C=O
DMF

Conditions

Temperature
55°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturecooled to room temperature
  2. 2
    workup.STIRRINGstirred vigorously for 20 minutes
  3. 3
    FiltrationPrecipitate was collected by filtration
  4. 4
    Washwashed with water
  5. 5
    Otherdried

Procedure

(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.v1Patent: US09095575B2uspto-grants-2015_08