Sodium Hydroxide → HCID 68487898, compound

HRID 1616547Notes

Reaction equation

HRID 1616547 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[S:13][C:14]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[OH:24])=[CH:15][N:16]=1>O.CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([OH:24])=[C:17]([C:14]2[S:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:25])=[O:4])=[N:16][CH:15]=2)[CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68492644HCID 68492644, compound

Product 1

HCID 68487898HCID 68487898, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add a solution of sodium hydroxide (2.60 g, 65 mmol) in water (50 mL) to a solution of 7-[5-(5-chloro-2-hydroxyphenyl)thiazol-2-yl]heptanoic acid methyl ester (5.76 g, 16 mmol) in methanol (100 mL) at 0° C. under nitrogen, warm the mixture to room temperature, and stir for a total of 1.5 hours. Remove the solvent under reduced pressure, dilute the residue with water (200 mL), cool to 0° C., and acidify to pH 1 with 1 N HCl. Collect the precipitate by filtration to afford 7-[5-(5-chloro-2-hydroxyphenyl)thiazol-2-yl]heptanoic acid (5.21 g, 95%): APCI mass spectrum m/z 338 [C16H18ClNO3S—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (200 mL)
  3. temperaturecool to 0° C.
  4. customCollect the precipitate
  5. filtrationby filtration

Sources & evidence

ORD record
ord-fe2830a2c9d04fa092d6c14f2f9a0cf1
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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