Sodium Hydroxide → 1-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

HRID 1942717Notes

Reaction equation

HRID 1942717 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([O:30]C)=[O:29])[CH2:25]4)[CH:20]=[CH:21][CH:22]=3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH-].[Na+]>C(O)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:32][CH3:33])=[C:19]([CH:20]=[CH:21][CH:22]=3)[CH2:23][N:24]3[CH2:25][CH:26]([C:28]([OH:30])=[O:29])[CH2:27]3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58494145HCID 58494145, compound

Product 1

HCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of methyl 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylate (2.78 g, 5.32 mmol) in Isopropanol (20.00 mL) and Water (10 mL) was added sodium hydroxide (0.638 g, 15.96 mmol). The mixture was stirred at rt for 51 mins. Stirring was stopped and the solution was concentrated under the reduced pressure. The residue was adjusted to pH value around 6 with HCl (1.0 M) solution, 1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid (2.33 g) was collected by filtering and dried in vacuum as yellow solid.

Workup

  1. stirringStirring
  2. concentrationthe solution was concentrated under the reduced pressure
  3. customwas collected
  4. filtrationby filtering
  5. customdried in vacuum as yellow solid

Sources & evidence

ORD record
ord-fa6f57cb33504937931f760c4260a325
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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