Sodium Azide → HCID 71182984, compound

HRID 2039393Notes

Reaction equation

HRID 2039393 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]([CH:12]1[C:28]2([CH3:29])[CH:15]([CH:16]3[CH:25]([CH2:26][CH2:27]2)[C:24]2([CH3:30])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)=[O:11])=[O:7].[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C)C=O>[N:32]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]([CH:12]1[C:28]2([CH3:29])[CH:15]([CH:16]3[CH:25]([CH2:26][CH2:27]2)[C:24]2([CH3:30])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)=[O:11])=[O:7])=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86762122HCID 86762122, compound

Product 1

HCID 71182984HCID 71182984, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 8 (325 mg, 0.639 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added sodium azide (415 mg, 6.39 mmol). The reaction mixture was heated to 65° C. and stirred overnight. Excess sodium azide was filtered off and the solvent was removed by rotary evaporation. The crude residue was dissolved in ethyl acetate and washed with water three times. The organic layer was dried over sodium sulfate and concentrated followed by flash chromatography in hexanes/ethyl acetate (4:3) to give 10 (206 mg, 71%). 1H NMR (500 MHz, CD3CN) δ 5.62 (1H, s, 4-H), 4.72 (1H, d, J=17, COCH2O), 4.53 (1H, d, J=17, COCH2O), 3.31 (2H, t, J=6.5, CH2N3), 2.55-0.99 (complex, 26H), 1.17 (3H, s, CH3), 0.64 (3H, s, CH3); 13C NMR (125 MHz, CD3CN) δ 204.49, 199.18, 173.04, 171.81, 123.86, 69.81, 59.25, 56.55, 54.21, 51.43, 44.95, 39.12, 38.60, 36.20, 35.94, 34.28, 33.36, 32.96, 32.52, 28.46, 24.79, 23.62, 23.07, 21.46, 17.35, 13.20. ESI-MS m/z [M+Na]+ observed: 478.3, calculated: 478.3.

Workup

  1. filtrationExcess sodium azide was filtered off
  2. customthe solvent was removed by rotary evaporation
  3. dissolutionThe crude residue was dissolved in ethyl acetate
  4. washwashed with water three times
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f720122df3624a9d9d0ab60c83b968b2
Source dataset
uspto-grants-2013_11
Patent number
US08580231B2

Reaction notes

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