Hydrochloric Acid → HCID 68297661, compound

HRID 1410901Notes

Reaction equation

HRID 1410901 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:6]=1[CH2:22][N:23]([CH2:34][C:35]([O:37][CH3:38])=[O:36])S(C1C=CC(C)=CC=1)(=O)=O)=O.C[O-].[Na+].Cl>CO>[CH3:38][O:37][C:35]([C:34]1[C:3]([OH:2])=[C:5]2[C:6](=[CH:22][N:23]=1)[N:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C:8](=[O:12])[C:9]([Br:11])=[CH:10]2)=[O:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86714144HCID 86714144, compound

Product 1

HCID 68297661HCID 68297661, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-1-(4-methoxy-benzyl)-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (2.03 g, 3.34 mmol) was dissolved in 80 mL of MeOH and placed in ice bath. NaOMe solution (2.3 mL, 10.0 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 (0-20% EtOAc/CH2Cl2) to give 1.02 g of the title compound as an off-white solid. MS: (+) m/z 419.19, 421.14 (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 (0-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-adcae98878204607a11e22dfa2a1414a
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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