Sodium Azide → HCID 54107403, compound

HRID 1872794Notes

Reaction equation

HRID 1872794 reaction equation
CS(O[C@H:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][C:8]([NH2:10])=[O:9])(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([C@@H:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][C:8]([NH2:10])=[O:9])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54329957HCID 54329957, compound

Product 1

HCID 54107403HCID 54107403, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-3-methanesulfonyloxyhexadecanamide (32 mg) and sodium azide (12 mg) in N,N-dimethylformamide (1 ml) was heated at 60° C. for 2 hours. The cooled mixture was partitioned between ethyl acetate (20 ml) and water (10 ml). The organic phase was washed with water (10 ml), and brine (10 ml), dried, and concentrated under vacuum, then the residue was recrystallized at -20° C. from a mixture of ethyl acetate (0.2 ml) and n-hexane (2 ml) to give (S)-3-azidohexadecanamide (14 mg).

Workup

  1. customThe cooled mixture was partitioned between ethyl acetate (20 ml) and water (10 ml)
  2. washThe organic phase was washed with water (10 ml), and brine (10 ml)
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customthe residue was recrystallized at -20° C. from a mixture of ethyl acetate (0.2 ml) and n-hexane (2 ml)

Sources & evidence

ORD record
ord-cf120db6dffa41ceb59a68ac89da37e0
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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