反应 #595319

ord-8364dc09c1dc4d2d89d557ecc4b19c5d

反应方程式

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

反应物

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

试剂

无

溶剂

CN(C)C=O
DMF

反应条件

温度
55°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度cooled to room temperature
  2. 2
    workup.STIRRINGstirred vigorously for 20 minutes
  3. 3
    过滤Precipitate was collected by filtration
  4. 4
    洗涤washed with water
  5. 5
    其他dried

实验过程

(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).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09095575B2uspto-grants-2015_08