Sodium Azide → HCID 86587220, compound

HRID 987131Notes

Reaction equation

HRID 987131 reaction equation
CS(O[CH2:6][C@@H:7]([O:32][CH2:33][CH3:34])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)(=O)=O.[N-:35]=[N+]=[N-].[Na+].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CN(C=O)C.C(OCC)C>[NH2:35][CH2:6][C@@H:7]([O:32][CH2:33][CH3:34])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 9957357HCID 9957357, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86587220HCID 86587220, compoundYield 174.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(2S)-3-[4-(2-{4-[(tert-Butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropyl methanesulfonate (described in Example 4a) (0.43 g, 0.87 mmole) was dissoved in dry DMF (5 ml). Sodium azide (0.23 g, 3.50 mmole) was added and the reaction mixture was heated to 80° C. and stirred overnight. The reaction was quenched with water and extracted with diethyl ether. The organic phase was washed with water, dried with magnesium sulfate and evaporated. The crude product was dissolved in dry diethyl ether and added to a solution of LAH (0.10 g, 2.62 mmole) in dry diethyl ether (50 ml). After one hour the reaction was quenched with water (0.5 ml), 5 M NaOH (1 ml) and water (0.5 ml) again. The mixture was refluxed for half an hour and the white precipitate was filtered off and the filtrate dried with magnesium sulfate and evaporated giving 0.63 g (72% yield) of the product.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. dissolutionThe crude product was dissolved in dry diethyl ether
  7. customAfter one hour the reaction was quenched with water (0.5 ml), 5 M NaOH (1 ml) and water (0.5 ml) again
  8. temperatureThe mixture was refluxed for half an hour
  9. filtrationthe white precipitate was filtered off
  10. dry with materialthe filtrate dried with magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-1d80dd0ee95f45739c78228edb8c9301
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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