Sodium Azide → HCID 86662085, compound

HRID 1959456Notes

Reaction equation

HRID 1959456 reaction equation
[C:1]([O:5][C:6]([N:8]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[C:9]1[N:10]=[CH:11][C:12]([N:36]2[CH2:40][C@@H:39]3[CH2:41][CH2:42][CH:43](CS([O-])(=O)=O)[C@H:38]3[CH2:37]2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:56]=[N+:57]=[N-:58].[Na+]>CN(C=O)C>[N:56]([CH:43]1[C@@H:38]2[CH2:37][N:36]([C:12]3[N:13]=[C:14]([C:15]4[O:16][C:17]([C:20]5[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:28])[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[CH:22][CH:21]=5)=[N:18][N:19]=4)[C:9]([N:8]([C:49]([O:51][C:52]([CH3:54])([CH3:53])[CH3:55])=[O:50])[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[N:10][CH:11]=3)[CH2:40][C@@H:39]2[CH2:41][CH2:42]1)=[N+:57]=[N-:58]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86662086HCID 86662086, compound

Product 1

HCID 86662085HCID 86662085, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [(3aR,6aS)-2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-6-yl]methanesulfonate (460 mg, 0.58 mmol) and sodium azide (190 mg, 573 μL, 2.9 mmol) in DMF (4 mL) was heated at 70° C. for 48 h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with H2O, followed by washing with brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to obtain tert-butyl N-[[4-[5-[6-[(3aR,6aS)-6-azido-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-[bis(tert-butoxycarbonyl)amino]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (401 mg, 93%). LC/MS m/z 733.7 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed with H2O
  4. washby washing with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f3f72acc8f342c6b6744b413d378580
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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