HCID 86662085, compound → HCID 66744634, compound

HRID 1959457Notes

Reaction equation

HRID 1959457 reaction equation
[N:1]([CH:4]1[C@@H:8]2[CH2:9][N:10]([C:12]3[N:17]=[C:16]([C:18]4[O:22][C:21]([C:23]5[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:25][CH:24]=5)=[N:20][N:19]=4)[C:15]([N:39]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[N:14][CH:13]=3)[CH2:11][C@@H:7]2[CH2:6][CH2:5]1)=[N+]=[N-]>[Pd]>[NH2:1][CH:4]1[C@@H:8]2[CH2:9][N:10]([C:12]3[N:17]=[C:16]([C:18]4[O:22][C:21]([C:23]5[CH:28]=[CH:27][C:26]([CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:25][CH:24]=5)=[N:20][N:19]=4)[C:15]([N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])=[N:14][CH:13]=3)[CH2:11][C@@H:7]2[CH2:6][CH2:5]1

Participants

3

Reactant 1

HCID 86662085HCID 86662085, compound

Product 1

HCID 66744634HCID 66744634, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with 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 (400 mg, 0.55 mmol) and Pd/C (108 mg, 1.0 mmol) was flushed under N2 followed by evacuating under vacuum. EtOH (3 mL) was added under inert atmosphere followed by evacuating under vacuum. The reaction mixture was stirred for 4.5 h under an atmosphere of H2. The reaction mixture was filtered and the solvent was evaporated under reduced pressure to obtain tert-butyl N-[[4-[5-[6-[(3aR,6aS)-6-amino-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 (300 mg, 78%). LC/MS m/z 707.5 [M+H]+.

Workup

  1. customwas flushed under N2
  2. customby evacuating under vacuum
  3. additionEtOH (3 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d9ae77ee2adc498593785688db5aca65
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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