Ammonium Hydroxide → HCID 68574067, compound

HRID 1429249Notes

Reaction equation

HRID 1429249 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:19]([CH3:21])[CH3:20])[C:7]([N:9]1[C@H:14]([C:15](O)=[O:16])[CH:13]2[CH2:18][CH:10]1[CH2:11][CH2:12]2)=[O:8])=[O:4].C([N:25](C(C)C)CC)(C)C.[OH-].[NH4+]>C(#N)C.O>[C:15]([C@@H:14]1[CH:13]2[CH2:18][CH:10]([CH2:11][CH2:12]2)[N:9]1[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:19]([CH3:21])[CH3:20])(=[O:16])[NH2:25]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 59616761HCID 59616761, compound

Product 1

HCID 68574067HCID 68574067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(3S)-2-((S)-2-(Methoxycarbonylamino)-3-methylbutanoyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (1.78 g, 5.97 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate (2.49 g, 5.56 mmol), and diisopropylethylamine (2.61 mL, 14.92 mmol) were dissolved in acetonitrile (30 mL) at ambient temperature and treated by dropwise addition with 28% ammonium hydroxide solution (2.49 g, 17.98 mmol). The resulting mixture was stirred for 1 hour and then diluted with water and extracted into dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give methyl (2S)-1-((3S)-3-carbamoyl-2-azabicyclo[2.2.1]heptan-2-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a white waxy solid.

Workup

  1. extractionextracted into dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aba82b37a8dc45c8aac4d247eb79ed30
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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