Hydrochloric Acid → 2-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid

HRID 2075501Notes

Reaction equation

HRID 2075501 reaction equation
C[O:2][C:3](=[O:34])[C:4]([CH3:33])([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:25][CH:26]=1)=[O:8])[CH3:5].[OH-].[Na+].O.Cl>C1COCC1.CO>[CH3:33][C:4]([NH:6][C:7]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[O:19][CH2:20][C:21]1[CH:22]=[N:23][C:24]([O:27][CH2:28][C:29]([F:31])([F:32])[F:30])=[CH:25][CH:26]=1)=[O:8])([CH3:5])[C:3]([OH:34])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 667010892-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester

Product 1

HCID 116483172-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acidYield 35.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 124 mg 2-methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester in 4 mL THF and 1 mL methanol was added 1.3 mL of 1M aqueous sodium hydroxide solution. After stirring at room temperature for 1 h the mixture was poured into cold water, acidified to pH 2 with 2 M 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 diisopropylether to yield 43 mg of 2-methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-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 diisopropylether

Sources & evidence

ORD record
ord-538cd97eb0c14ed0b61810e8dd40ea4b
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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