Sodium Hydroxide → HCID 57864014, compound

HRID 1889273Notes

Reaction equation

HRID 1889273 reaction equation
C[O:2][C:3](=[O:32])[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][CH2:22][O:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=1)=[O:9])([CH3:6])[CH3:5].[OH-].[Na+]>CO>[F:30][C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([F:31])[CH:27]=1)[O:23][CH2:22][CH2:21][O:20][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:32])=[O:2])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68840887HCID 68840887, compound

Product 1

HCID 57864014HCID 57864014, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22 mg 2-({1-[2-(3,5-difluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid methyl ester were reacted with 0.2 ml of 2 M sodium hydroxide in 1 ml methanol at 65° C. for 1 h. The organic solvents were then removed in vacuo, and the residue was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulphate, and concentrated. After recrystallization from n-heptane 3 mg of 2-({1-[2-(3,5-difluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid were obtained.

Workup

  1. customThe organic solvents were then removed in vacuo
  2. extractionextracted with ethyl acetate twice
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated
  5. customAfter recrystallization from n-heptane 3 mg of 2-({1-[2-(3,5-difluoro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-2-methyl-propionic acid
  6. customwere obtained

Sources & evidence

ORD record
ord-c48b832b27a3454c9bae83a39fc2e546
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…