Реакция #595319

ord-8364dc09c1dc4d2d89d557ecc4b19c5d

Уравнение реакции

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

Реактанты

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

Реагенты

Нет

Растворители

CN(C)C=O
DMF

Условия реакции

Температура
55°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураcooled to room temperature
  2. 2
    workup.STIRRINGstirred vigorously for 20 minutes
  3. 3
    ФильтрацияPrecipitate was collected by filtration
  4. 4
    Промывкаwashed with water
  5. 5
    Другоеdried

Методика

(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).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09095575B2uspto-grants-2015_08