Hydrochloric Acid → [Rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid

HRID 1726972Notes

Reaction equation

HRID 1726972 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]([CH3:38])[CH:18]([C:21]2[C:22]([CH3:37])=[N:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)=[CH:25][CH:26]=2)[CH2:19][CH3:20])=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:38][N:17]([CH:18]([C:21]1[C:22]([CH3:37])=[N:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=2)=[CH:25][CH:26]=1)[CH2:19][CH3:20])[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([O:6][CH2:5][C:4]([OH:39])=[O:3])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69036795[Rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester

Product 1

HCID 11489062[Rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

0.042 g (0.078 mmol) of the above prepared [rac]-[4-(methyl-{1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-propyl}-amino)-naphthalen-1-yloxy]-acetic acid ethyl ester was dissolved in 0.84 ml of THF/EtOH=1/1, treated at 0° C. with 0.24 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 2 h. The reaction mixture was then neutralized with HCl dil. to pH 7, extracted with AcOEt, the organic layer was washed with water, dried over sodium sulfate, and evaporated to dryness to leave, after crystallization from AcOEt/hekane, 0.033 g of the title compound as yellowish crystals of mp. 76-78° C.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customto leave
  6. customafter crystallization from AcOEt/hekane, 0.033 g of the title compound as yellowish crystals of mp. 76-78° C.

Sources & evidence

ORD record
ord-046511912399458b936801c4569d4cb7
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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