Acetic Acid → HCID 69293416, compound

HRID 2117550Notes

Reaction equation

HRID 2117550 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+:48].C(O)(=O)C>CCOC(C)=O.O>[Na+:48].[C:33]1([S:30]([N:16]([CH2:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][CH2:7][C:6]([O-:39])=[O:5])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:22][CH:23]=2)(=[O:31])=[O:32])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 54043815HCID 54043815, compound

Product 1

HCID 69293416HCID 69293416, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared following the method described in Example 3, Step C from (3-{[benzenesulfonyl-(4-pyridin-2-yl-benzyl)-amino]-methyl}-phenoxy)-acetic acid tert-butyl ester of Step B. The TFA salt was diluted with EtOAc and water and the aqueous solution was basified to about pH 11 with NaOH (1N). The aqueous solution was acidified with glacial acetic acid to about pH 5 and was washed with EtOAc (3×). The organic solution was dried (MgSO4), filtered, and concentrated, azeotroping with toluene, to provide the free acid (128 mg). The acid was dissolved in a mixture of acetone (4 mL), MeOH (4 mL) and water (0.5 mL), and NaHCO3 (22 mg, 0.258 mmol) was added. The reaction was stirred for 24 h and was concentrated in vacuo, azeotroping with EtOH (3×) and CHCl3 (1×) to provide the title sodium salt (137 mg). 1H NMR (400 MHz, CD3OD) δ 8.56 (dd, 1H), 7.89-7.76 (m, 6H), 7.65-7.56 (m, 3H), 7.33 (m, 1H), 7.21 (d, 2H), 7.05 (t, 1H), 6.74 (d, 1H), 6.63 (m, 2H), 4.40 (s, 2H), 4.31 (s, 2H), 4.21 (s, 2H); MS 487 (M−1).

Workup

  1. washwas washed with EtOAc (3×)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customazeotroping with toluene

Sources & evidence

ORD record
ord-c048ef9b143747009603f4204d032505
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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