Acetic Acid → HCID 86666882, compound

HRID 510970Notes

Reaction equation

HRID 510970 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[C:12]([O:29][CH3:30])=[C:13]([C:19]2[N:24]=[C:23]([C:25]([O:27]C)=[O:26])[CH:22]=[CH:21][CH:20]=2)[C:14]([CH3:18])=[C:15]([Cl:17])[CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].C(O)(=O)C>CO.O.C(#N)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[C:12]([O:29][CH3:30])=[C:13]([C:19]2[N:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[CH:21][CH:20]=2)[C:14]([CH3:18])=[C:15]([Cl:17])[CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86666883HCID 86666883, compound

Product 1

HCID 86666882HCID 86666882, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The methyl 6-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)pyridine-2-carboxylate (0.075 g, 0.17 mmol) was dissolved in methanol (5.0 mL) and the lithium hydroxide-monohydrate (0.022 g, 0.52 mmol) dissolved in water (0.5 mL) was added. The reaction was stirred at room temperature and monitored by LC/MS. After stirring for 18 h the reaction was complete. Acetic acid was added to adjust the pH 5 and the reaction was concentrated to give a semisolid residue. The crude was diluted with acetonitrile and concentrated 3× to remove residual water and finally give 6-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)pyridine-2-carboxylic acid as a crude solid residue. LCMS calculated for C17H18ClN2O5(M+H)+: m/z=365.1. found: 365.0.

Workup

  1. additionwas added
  2. stirringAfter stirring for 18 h the reaction
  3. concentrationthe reaction was concentrated
  4. customto give a semisolid residue
  5. concentrationconcentrated 3×
  6. customto remove residual water and finally give 6-(3-{1-[(tert-butoxycarbonyl)amino]ethyl}-5-chloro-2-methoxy-6-methylphenyl)pyridine-2-carboxylic acid as a crude solid residue

Sources & evidence

ORD record
ord-86c8e691d4254bbf8e20e6b2aa5c3633
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…