Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59229153, compound

HRID 2065858Notes

Reaction equation

HRID 2065858 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]([OH:15])=O)[CH2:11][S:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:21]([O:25][N:26]1N=NC2C=CC=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.Cl.CNOC.C(N(CC)C(C)C)C>CN(C=O)C>[CH3:21][O:25][N:26]([CH3:27])[C:13]([CH:12]1[CH2:11][S:10][C:9]([CH3:17])([CH3:16])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15]

Participants

7

Reactant 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 181649HOAtHCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14393882HCID 14393882, compound

Product 1

HCID 59229153HCID 59229153, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flask containing 3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid (see Suaifan et al., Tetrahedron 62, 11245-11266 (2006); Kemp and Carey, J. Org. Chem. 54, 3640 (1989)) (4 g, 0.015 mol), HATU (7.3 g, 0.019 mol), HOAt (28 ml of 0.6M, 0.017 mol), N,O-dimethylhydroxylamine-HCl (2.92 g, 0.03 mol), diethylisopropylamine (5.1 L, 0.03 mol), and DMF (20 mL) was stirred at room temp for 17 h. Solvent was evaporated, and the residue was portioned between EtOAc (200 mL) and water (300 mL). The aqueous layer was extracted with EtOAc (50 mL), and the combined organic layers washed with 30% citric acid solution (2×100 mL), saturated bicarbonate (2×100 mL), and brine (1×50 mL). After evaporation, the crude residue was chromatographed on normal phase silica—eluting with heptane/EtOAc (2/1) to yield 3.84 g (84%) solid.

Workup

  1. customSolvent was evaporated
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  3. washthe combined organic layers washed with 30% citric acid solution (2×100 mL), saturated bicarbonate (2×100 mL), and brine (1×50 mL)
  4. customAfter evaporation
  5. customthe crude residue was chromatographed on normal phase silica—
  6. washeluting with heptane/EtOAc (2/1)

Sources & evidence

ORD record
ord-841ac262c22f46aea3bcf607e9c5e3e7
Source dataset
uspto-grants-2012_10
Patent number
US08288559B2

Reaction notes

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