Methylamine → 6-(Benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid

HRID 1846838Notes

Reaction equation

HRID 1846838 reaction equation
[C:1]1([S:7]([CH:10]([NH2:29])[C:11]2O[C:15]([C:17]([OH:19])=[O:18])=[C:14]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13](=[O:28])[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][NH2:31]>CO>[C:1]1([S:7]([CH:10]([NH2:29])[C:11]2[N:31]([CH3:30])[C:15]([C:17]([OH:19])=[O:18])=[C:14]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:13](=[O:28])[CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 867256956-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid

Product 1

HCID 867256966-(Benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acidYield 65.08%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (12-01) (640.0 mg, 1.54 mmol) in MeOH (5.0 mL) was added methylamine (2 M in methanol, 2.0 mL) at room temperature and the mixture was stirred for 6 h at room temperature. After completion of the reaction, the solvent was removed under reduced pressure to get the crude compound. It was then purified using normal column chromatography to get 6-(benzene sulfonyl amino-methyl)-3-benzyloxy-1-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (13-01) (430.0 mg, 65.08%) as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customto get the crude compound
  4. customIt was then purified

Sources & evidence

ORD record
ord-3dafafba2ed348fa8dff6688e0d65a7c
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

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