Sodium Azide → HCID 60077744, compound

HRID 2084540Notes

Reaction equation

HRID 2084540 reaction equation
[N-:1]=[N+]=[N-].[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:23]=[CH:22][C:21]([NH2:1])=[CH:20][CH:19]=1)[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 60077753HCID 60077753, compound

Product 1

HCID 60077744HCID 60077744, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium azide (1.26 g, 19.4 mmol) was added to a solution of [1(S)-(4-fluorobenzoyl)-2,2-dimethylpropyl]-carbamic acid tert-butyl ester (0.20 g, 0.7 mmol) in DMF (15 mL), and the mixture heated at 120° C. for 40 hours. The solvent was removed in vacuo before addition of 10% NaHCO3 (aq.) (30 mL) to the residual solid. The aqueous phase was extracted with ethyl acetate (2×30 mL) and the organic phases washed with brine (1×30 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a yellow solid. Purification by column chromatography (SiO2, 4:1 iso-hexane:ethyl acetate) afforded the title compound as a yellow solid (67 mg, 36%).

Workup

  1. customThe solvent was removed in vacuo before addition of 10% NaHCO3 (aq.) (30 mL) to the residual solid
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×30 mL)
  3. washthe organic phases washed with brine (1×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customto give a yellow solid
  8. customPurification by column chromatography (SiO2, 4:1 iso-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ece5bd87f80c4882af4369f7856d4450
Source dataset
uspto-grants-2004_04
Patent number
US06716878B1

Reaction notes

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