Sodium Azide → HCID 54340169, compound

HRID 355507Notes

Reaction equation

HRID 355507 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:20][C@H:19]([CH2:21][O:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:9]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@@H:8]2[F:31])[CH:5]=[N:4][C:3]=1[C:32](=[O:35])[CH2:33]Cl.[N-:36]=[N+:37]=[N-:38].[Na+]>CN(C)C=O>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:20][C@H:19]([CH2:21][O:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:9]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@@H:8]2[F:31])[CH:5]=[N:4][C:3]=1[C:32](=[O:35])[CH2:33][N:36]=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53781734HCID 53781734, compound2×

Product 1

HCID 54340169HCID 54340169, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound (16) obtained in step (7) above (185 mg) was dissolved in N,N-dimethylformamide (3.7 ml), to which was then added sodium azide (37 mg), and the resultant mixture was stirred at room temperature for 1 hour to effect the desired reaction in order to convert the chloro group of compound (16) into azido group and thus to produce the titled compound (17). The reaction solution was concentrated and the residue obtained was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate and then concentrated to yield a yellow syrup. This syrup was purified by silica gel column chromatography (developer solvent:toluene-ethyl acetate, 1:1), to give the titled compound (17) as a colorless solid (176 mg). Yield: 94%.

Workup

  1. customreaction in order

Sources & evidence

ORD record
ord-2ecf18526d224ca29d819c92a2857d49
Source dataset
uspto-grants-1998_11
Patent number
US05831072

Reaction notes

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