N,O-Dimethylhydroxylamine → HCID 86671822, compound

HRID 536992Notes

Reaction equation

HRID 536992 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][NH:17][O:18][CH3:19].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13](=[O:15])[N:17]([O:18][CH3:19])[CH3:16])[CH2:10][CH2:11][CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86671822HCID 86671822, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid (3 g, 13.94 mmol) in dry DMF (50 mL) was added N,O-dimethylhydroxylamine x HCl (1.36 g, 13.94 mmol) and DIEA (9.21 mL, 55.75 mmol). The reaction flask was cooled to 0° C. and after 10 minutes HATU (5.30 g, 13.94 mmol) was added to the solution (which turned yellow on addition). After 2 hrs the DMF was removed by rotary evaporation at reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution. The organic phase was dried with Na2SO4, filtered and evaporated on silica. The product was purified by flash chromatography (heptane: ethyl acetate (1:1) to give the product as a colourless oil that slowly crystallizes (3.13 g) in 87% yield.

Workup

  1. additionwas added to the solution (which turned yellow on addition)
  2. customAfter 2 hrs the DMF was removed by rotary evaporation at reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed twice with 10% citric acid (aq) and saturated NaHCO3(aq) solution
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated on silica
  8. customThe product was purified by flash chromatography (heptane: ethyl acetate (1:1)

Sources & evidence

ORD record
ord-cc2b44842334443cae2b9a779cdf8194
Source dataset
uspto-grants-2014_10
Patent number
US08859605B2

Reaction notes

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