Hydrochloric Acid → HCID 66745393, compound

HRID 1959468Notes

Reaction equation

HRID 1959468 reaction equation
[C:1]([O:5][C:6]([N:8]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:9]1[C:10]([C:25]2[O:29][C:28]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][N:37]([CH3:45])[C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:32][CH:31]=3)=[N:27][N:26]=2)=[N:11][C:12]([C:15]2[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH:16]=2)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CCOC(C)=O>[C:49]([O:48][C:46]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]1[C:10]([C:25]2[O:29][C:28]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][N:37]([CH3:45])[C:38](=[O:44])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[CH:32][CH:31]=3)=[N:27][N:26]=2)=[N:11][C:12]([C:15]2[CH2:24][CH2:23][C:18](=[O:19])[CH2:17][CH:16]=2)=[CH:13][N:14]=1)=[O:47])([CH3:50])([CH3:51])[CH3:52]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66744427HCID 66744427, compound

Product 1

HCID 66745393HCID 66745393, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (680 mg, 0.94 mmol) in THF (2.0 mL) was added 1M aqueous HCl (1.9 mL of 1 M, 1.9 mmol) and the reaction mixture was heated at 60° C. for 6 h. The reaction was cooled to room temperature and diluted with EtOAc, the layers were separated and the organic layer was washed once with aqueous NaHCO3, then once with brine, dried over Na2SO4, filtered and concentrated to dryness to yield tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-oxocyclohexen-1-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (487 mg, 76%) and was used without further purification. LC/MS m/z 677.5 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe layers were separated
  3. washthe organic layer was washed once with aqueous NaHCO3
  4. dry with materialonce with brine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-32db77afbe6b4631a47214701f41163b
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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