Sodium Azide → Azido-PEG6-C1-Boc

HRID 1726833Notes

Reaction equation

HRID 1726833 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10](=[O:31])[CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29]Br)([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10](=[O:31])[CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][N:1]=[N+:2]=[N-:3])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86616366Br-PEG6-CH2COOtBu

Product 1

HCID 10905931Azido-PEG6-C1-BocYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (1.5 g, 23 mmol) was added to a solution of compound 3 (1.9 g, 4.1 mmol) in dry DMF (50 mL) and the resulting mixture was stirred at 80° C. overnight. The reaction mixture was concentrated in vacuo and then triturated with CH2Cl2 (20 mL) and filtered to remove sodium azide. The filtrate was concentrated in vacuo and the residue was loaded onto a silica gel gravity column (200 g) and eluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v) to afford compound 4 as a colorless oil (1.0 g, 57%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with CH2Cl2 (20 mL)
  3. filtrationfiltered
  4. customto remove sodium azide
  5. concentrationThe filtrate was concentrated in vacuo
  6. washeluted with CH2Cl2:MeOH 100:0 to 20:1 (v/v)

Sources & evidence

ORD record
ord-4bcfd1eec923431f919e1cbd0bf9dcb2
Source dataset
uspto-grants-2009_02
Patent number
US07494714B2

Reaction notes

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