Hydrochloric Acid → HCID 11589278, compound

HRID 2062072Notes

Reaction equation

HRID 2062072 reaction equation
C[O:2][C:3](=[O:30])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][C:22]1[CH:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)=[O:9])([CH3:6])[CH3:5].[OH-].[Na+].O.Cl>C1COCC1.CO>[CH3:29][O:28][C:25]1[N:24]=[CH:23][C:22]([CH2:21][O:20][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][C:10]=2[C:8]([NH:7][C:4]([CH3:6])([CH3:5])[C:3]([OH:30])=[O:2])=[O:9])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66701063HCID 66701063, compound

Product 1

HCID 11589278HCID 11589278, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 191 mg 2-{[1-(6-Methoxy-pyridin-3-ylmethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester in 6 mL THF and 1 mL methanol was added 2.3 mL of 1 M aqueous sodium hydroxide solution. After stirring at room temperature for 4 h the mixture was poured into cold water, acidified to pH 4 with 2M HCl and extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulphate, filtrated and concentrated to provide a yellow oil, which could be crystallized from diethylether and methanol to yield 44 mg of 2-{[1-(6-methoxy-pyridin-3-ylmethoxy)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customto provide a yellow oil, which
  6. customcould be crystallized from diethylether and methanol

Sources & evidence

ORD record
ord-98b34a63d6e54e0f9e4560c07f616d3a
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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