Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 47451638, compound

HRID 1850144Notes

Reaction equation

HRID 1850144 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][O:17][NH:18][CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:16][O:17][N:18]([CH3:19])[C:10](=[O:12])[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 47451638HCID 47451638, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(tert-butoxycarbonylamino)-2-methylpropanoic acid (6.62 g, 32.6 mmol), O,N-dimethylhydroxylamine hydrochloride (3.50 g, 35.8 mmol), and HATU (14.86 g, 39.1 mmol) were combined in DMF (100 mL). To this solution was added Hunig's Base (17.07 mL, 98 mmol). The reaction was stirred for overnight (17 hours). The reaction was then concentrated under vacuum and the residue was diluted with EtOAc (300 mL) and washed with water (2×80 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified via silica gel flash chromatography (10-50 percent EtOAc-Hexanes) to afford the desired product as a white solid (6.36 g). LCMS m/z 247.2 (M+H)+, Rt 0.61 min.

Workup

  1. concentrationThe reaction was then concentrated under vacuum
  2. additionthe residue was diluted with EtOAc (300 mL)
  3. washwashed with water (2×80 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via silica gel flash chromatography (10-50 percent EtOAc-Hexanes)

Sources & evidence

ORD record
ord-69aa773912004ec09cb72af9f8834e2f
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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