Hydrochloric Acid → HCID 68297632, compound

HRID 919881Notes

Reaction equation

HRID 919881 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=1[CH2:14][N:15]([CH2:26][C:27]([O:29][CH3:30])=[O:28])S(C1C=CC(C)=CC=1)(=O)=O)=O.C[O-].[Na+].Cl>CO>[CH3:30][O:29][C:27]([C:26]1[C:3]([OH:2])=[C:5]2[C:6](=[CH:14][N:15]=1)[N:7]([CH3:13])[C:8](=[O:12])[C:9]([Br:11])=[CH:10]2)=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 68297436HCID 68297436, compound

Product 1

HCID 68297632HCID 68297632, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (292 mg, 0.58 mmol) was dissolved in 10 mL of MeOH and placed in ice bath. NaOMe solution (0.4 mL, 1.75 mmol, 4.375 M in MeOH) was added and the mixture was stirred for 16 h at r.t. 0.1 M HCl was added to acidify the mixture, and the resulting suspension was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 150 mg of the title compound as an off-white solid. MS: (+) m/z 313.13, 315.14 (M+1, 79/81Br).

Workup

  1. extractionthe resulting suspension was extracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8039cc7457b041b4baf3cee60cedeb79
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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