Sodium Azide → HCID 86586727, compound

HRID 2088185Notes

Reaction equation

HRID 2088185 reaction equation
[C:1]([NH:4][C@@H:5]1[CH2:11][C@:10]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:6]1[CH2:7][CH2:8][C@H:9]2[O:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=1)(=O)[CH3:2].[N-:42]=[N+:43]=[N-:44].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[CH2:13]([N:12]1[C@@H:6]2[C@H:5]([N:4]3[C:1]([CH3:2])=[N:44][N:43]=[N:42]3)[CH2:11][C@@:10]1([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]([O:26][CH2:27][C:28]1[CH:29]=[C:30]([C:38]([F:40])([F:41])[F:39])[CH:31]=[C:32]([C:34]([F:36])([F:35])[F:37])[CH:33]=1)[CH2:8][CH2:7]2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 86586725HCID 86586725, compound

Product 1

HCID 86586727HCID 86586727, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,5S*,6R*)-6-Acetamido-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 109; 384 mg, 0.67 mmol) and sodium azide in dichloromethane (10 ml) were cooled to 0° C. and trifluoromethanesulphonic anhydride (0.11 ml, 0.67 mmol) added. The reaction was warmed to room temperature and stirred for 3 hours then quenched with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (×3). The organics were dried (MgSO4) and concentrated in vacuo to give a brown solid. This was purified by flash column chromatography [2.5% methanol in dichloromethane] to give the title compound as a cream-coloured solid (134 mg, 34%).

Workup

  1. customthen quenched with saturated sodium hydrogen carbonate solution
  2. extractionextracted with dichloromethane (×3)
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid
  6. customThis was purified by flash column chromatography [2.5% methanol in dichloromethane]

Sources & evidence

ORD record
ord-839e069a3b4f46b2a70d124dd3ea1b6d
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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