Sodium Azide → HCID 57771627, compound

HRID 2070578Notes

Reaction equation

HRID 2070578 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][C:20]3([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19]2)=[CH:12][CH:11]=1)[C:6]([NH:8][CH3:9])=O.[N-:30]=[N+:31]=[N-:32].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:29])[CH2:4][CH:5]([C:6]1[N:8]([CH3:9])[N:32]=[N:31][N:30]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][C:20]3([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 57771603HCID 57771603, compound

Product 1

HCID 57771627HCID 57771627, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methyl-3-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-succinamic acid methyl ester (178 mg) obtained in Step 7 in acetonitrile (5 mL) were added successively sodium azide (85 mg) and trifluoromethanesulfonic anhydride (0.29 mL), followed by stirring the reaction mixture at room temperature for 24 hours. Then, after addition of saturated aqueous sodium bicarbonate solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by thin-layer column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1) to give 3-(1-methyl-1H-tetrazol-5-yl)-3-[4-(spiro[5.5]undec-2-ylmethoxy)-phenyl]-propionic acid methyl ester (41 mg).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by thin-layer column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:1)

Sources & evidence

ORD record
ord-98b11829576c494c8327291b204e5dda
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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