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

HRID 1942711Notes

Reaction equation

HRID 1942711 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+].Cl>O1CCCC1.C(O)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]([CH2:23][N:24]4[CH2:25][CH:26]([C:28]([OH:30])=[O:29])[CH2:27]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]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 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 acidYield 105.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 (D13) (30.3 g, 62.3 mmol) in Tetrahydrofuran (THF) (200 mL), Ethanol (150 mL) and Water (60 mL) was added sodium hydroxide (4.99 g, 125 mmol). The reaction mixture was stirred at room temperature overnight. Then pH of the reaction mixture was adjusted with 6 N HCl until pH ˜2.0. White solid was precipitated. The organic solvent was removed in by rotary evaporator. The solid was collected through filtration. The solid was washed water (150 mL×3) and dried in vacuo to afford 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3 azetidinecarboxylic acid (31 g), which was used for the following procedure without further purification.

Workup

  1. customWhite solid was precipitated
  2. customThe organic solvent was removed in by rotary evaporator
  3. filtrationThe solid was collected through filtration
  4. washThe solid was washed water (150 mL×3)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9929a74fd5ce47bdb220a735333595b2
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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