Sodium Azide → HCID 21969021, compound

HRID 1420842Notes

Reaction equation

HRID 1420842 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]#[C:8][CH2:9][N:10]1[CH2:33][CH2:32][CH2:31][C@:12]2([O:16][CH2:15][C@H:14]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=3[O:27][CH:28]([CH3:30])[CH3:29])[CH2:13]2)[C@@H:11]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CS(C)=O.O>[N:1]([CH2:6][C:7]#[C:8][CH2:9][N:10]1[CH2:33][CH2:32][CH2:31][C@:12]2([O:16][CH2:15][C@H:14]([C:17]3[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[CH:19][C:18]=3[O:27][CH:28]([CH3:30])[CH3:29])[CH2:13]2)[C@@H:11]1[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 21969022HCID 21969022, compound

Product 1

HCID 21969021HCID 21969021, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium azide (15 mg) was added to a solution of (3S,5R,6S)-7-(4-chlorobut-2-yn-1-yl)-3-[2-isopropoxy-5-(trifluoromethyl)phenyl]-6-phenyl-1-oxa-7-aza-spiro[4,5]decane (Description 75, 100 mg) in dimethylsulfoxide (1 ml). The mixture was stirred at room temperature overnight, diluted with water (20 ml) and extracted with ether (3×5 ml). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under pressure to give the title compound as a colorless oil (98 mg). m/z (ES+) m/z 513 (M+1).

Workup

  1. extractionextracted with ether (3×5 ml)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under pressure

Sources & evidence

ORD record
ord-59e0982481054617a62a94ec4ebfcce2
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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