Sodium Hydroxide → HCID 22633491, compound

HRID 398189Notes

Reaction equation

HRID 398189 reaction equation
C([O:3][C:4](=[O:36])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[S:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Na+]>CCO>[C:27]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]([C:20]2[S:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:36])=[O:3])=[CH:10][CH:11]=3)[N:19]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69871227HCID 69871227, compound

Product 1

HCID 22633491HCID 22633491, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A sample of 2-{4-[2-(2-biphenyl-4-yl-5-methyl-thiazol-4-yl)-ethoxy]-phenoxy}-2-methyl-propionic acid ethyl ester (400 mg, 0.8 mmol) was dissolved in EtOH (15 mL) and 5N NaOH (5 mL) added. The reaction was warmed at 40° C. for 1.5 h and then cooled to room temperature. After removing some of the EtOH, the reaction was acidified with HCl. After stirring in an ice-bath for 1 h, the yellow solid was collected and dried to give 328 mg (87%) acid as a yellow powder, mp 174° C., MS (m/e) 474 (MH); 1H NMR (CDCl3) δ1.53 (s, 6H), 2.57 (s, 3H), 3.48 (t, 2H), 4.44 (t, 2H), 6.80 (d, 2H), 6.91 (d, 2H), 7.40-7.54 (m, 3H), 7.51 (d, 2H), 7.64 (d, 2H), 8.26 (d, 2H).

Workup

  1. temperaturecooled to room temperature
  2. customAfter removing some of the EtOH
  3. customthe yellow solid was collected
  4. customdried

Sources & evidence

ORD record
ord-38376adaa1c24b8b8a995aeabe0493fc
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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