Hydrochloric Acid → N-[[4-Bromo-1-[2-(4-fluorophenoxy)ethoxy]-2-naphthalenyl]carbonyl]-2-methylalanine

HRID 1889258Notes

Reaction equation

HRID 1889258 reaction equation
C[O:2][C:3](=[O:32])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[C:18]([Br:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:9])([CH3:6])[CH3:5].Cl>C1COCC1.[OH-].[Na+].CO>[Br:20][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[C:10]([C:8]([NH:7][C:4]([CH3:6])([CH3:5])[C:3]([OH:32])=[O:2])=[O:9])[CH:19]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68841391HCID 68841391, compound

Product 1

HCID 24769566N-[[4-Bromo-1-[2-(4-fluorophenoxy)ethoxy]-2-naphthalenyl]carbonyl]-2-methylalanine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

61 mg 2-({4-bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester in 0.5 ml THF, 0.36 ml of 2 M sodium hydroxide and 1.7 ml methanol were reacted in a microwave at 120° C. for 6 min. The reaction was then acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over magnesium sulphate, and concentrated. After purification of the residue by RP-HPLC 27 mg of 2-({4-bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid were obtained.

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customAfter purification of the residue by RP-HPLC 27 mg of 2-({4-bromo-1-[2-(4-fluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid
  5. customwere obtained

Sources & evidence

ORD record
ord-2cc396ab89324918b6e3f7ad630b51e9
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…