Sodium Hydroxide → HCID 448658, compound

HRID 457994Notes

Reaction equation

HRID 457994 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[O:29])[NH:15][CH2:16][C:17]1[S:18][C:19]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([F:28])[C:20]=2[N:21]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[O:29])[NH:15][CH2:16][C:17]2[S:18][C:19]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([F:28])[C:20]=3[N:21]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:30])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22093486HCID 22093486, compound

Product 1

HCID 448658HCID 448658, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (5-fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid ethyl ester (1 g, 2.3 mmol) in ethanol (11 mL) was treated with aq 2 N NaOH (6.8 mL, 14 mmol) and stirred at room temperature. After stirring for 1 h, the solution was concentrated in vacuo and acidified to pH 1 with aq 2 N HCl. The resulting solution was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried over MgSO4, filtered, and concentrated to give {5-fluoro-2[(4,5,7-trifluoro-benzothiazol-2-ylmethyl)carbamoyl]-phenoxy}-acetic acid. (0.68 g, 73%) as a white crystalline solid. mp 172–174° C.; Rf 0.38 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 13.25 (br s, 1 H), 9.49 (t, J=6 Hz, 1 H), 7.95 (dd, J1=9 Hz, J2=7.2 Hz, 1 H), 7.78–7.69 (m, 1 H), 7.11 (dd, J1=11.0 Hz, J2=2.3 Hz, 1 H), 6.94 (dd, J1=8.4 Hz, J2=2.4 Hz, 1 H), 4.94–4.92 (m, 4 H). ESI-LC/MS m/z calcd for C17H10F4N2O4S: 414.3. Found 413.0 (M−1)−. Anal. calcd for C17H10F4N2O4S: C, 49.28; H, 2.43; N, 6.76. Found C, 49.26; H, 2.47; N, 6.68.

Workup

  1. stirringAfter stirring for 1 h
  2. concentrationthe solution was concentrated in vacuo
  3. additionThe resulting solution was diluted with ethyl acetate
  4. washwashed with saturated NaCl
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e7af5ca0b5974585bbab4408671e2b58
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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