Methanamine, N-methoxy-, hydrochloride (1:1) → 5-Methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amide

HRID 559667Notes

Reaction equation

HRID 559667 reaction equation
[CH3:1][S:2]([C:5]1[O:9][C:8]([C:10]([OH:12])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CN([C:16]([O:20][N:21]1N=NC2C=CC=C[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNOC>CN(C=O)C.C(=O)(O)[O-].[Na+]>[CH3:16][O:20][N:21]([CH3:22])[C:10]([C:8]1[O:9][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=1)=[O:12]

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 545928165-Methanesulfonylfuran-2-carboxylic acid

Product 1

HCID 592784855-Methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-methanesulfonyl-furan-2-carboxylic acid (1.1 g, 5.8 mmol) in DMF (20 mL) was added HBTU (2.8 g, 8.7 mmol) and DIPEA (3.2 mL, 17.4 mmol). After stirring for 10 minutes, N,O-dimethylhydroxylamine hydrochloride (0.85 g, 0.71 mmol) was added. After 18 hours, the mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (4×25 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 5-methanesulfonyl-furan-2-carboxylic acid methoxy-methyl-amide.

Workup

  1. waitAfter 18 hours
  2. extractionextracted with ethyl acetate (4×25 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88ebb3747dc242d0a1a30df8bc443fc0
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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