Sodium Azide → HCID 60077760, compound

HRID 2084542Notes

Reaction equation

HRID 2084542 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10](=[O:26])[NH:11][C@H:12]([C:17](=[O:25])[C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10](=[O:26])[NH:11][C@H:12]([C:17](=[O:25])[C:18]1[CH:19]=[CH:20][C:21]([N:1]=[N+:2]=[N-:3])=[CH:22][CH:23]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:6])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 60077753HCID 60077753, compound

Product 1

HCID 60077760HCID 60077760, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium azide (37.9 g, 0.58 mol) was added to a solution of [1(S)-(4-fluorobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester (6.0 g, 19.4 mmol) in DMF (400 mL), and the mixture heated at 120° C. for 24 hours. The solvent was removed in vacuo and the residual solid taken up in ethyl acetate (200 ml). The organic phase was washed with 1M Na2CO3 (1×400 ml) and brine (1×400 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a yellow solid. Purification by column chromatography (SiO2, 6:1 iso-hexane:ethyl acetate) afforded the title compound as a yellow solid (1.96 g) and [1(S)-(4-Azidobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester as an orange solid (0.97 g) (47% combined yield).

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic phase was washed with 1M Na2CO3 (1×400 ml) and brine (1×400 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give a yellow solid
  7. customPurification by column chromatography (SiO2, 6:1 iso-hexane:ethyl acetate)
  8. customafforded

Sources & evidence

ORD record
ord-6d99e781385c403fb2dd4e3a1475ab3e
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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