Hydrochloric Acid → 1-[2-(2-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylic acid trifluoroacetate

HRID 1942722Notes

Reaction equation

HRID 1942722 reaction equation
[CH2:1]([C:3]1[C:8]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=3)=[N:12][N:13]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:28][CH2:29][N:30]1[CH2:33][CH:32]([C:34]([O:36]C)=[O:35])[CH2:31]1)[CH3:2].[OH-:38].[Na+].Cl.C([OH:44])(C)C>O>[F:25][C:24]([F:27])([F:26])[C:16]([OH:44])=[O:38].[CH2:1]([C:3]1[C:8]([C:9]2[S:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=3)=[N:12][N:13]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:28][CH2:29][N:30]1[CH2:31][CH:32]([C:34]([OH:36])=[O:35])[CH2:33]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 66981783Methyl 1-[2-(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylate

Product 1

HCID 866590181-[2-(2-Ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 1-[2-(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylate (D20) (25 mg) in isopropanol (2 mL) and water (2 mL) at room temperature was added sodium hydroxide (1.874 mg). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was neutralized with 1 M HCl solution. The solvent was removed in vacuo. The residue was dissolved in THF, and filtered. The filtrate was purified by Mass Directed AutoPrep to give 1-[2-(2-ethyl-3-{5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl}phenyl)ethyl]-3-azetidinecarboxylic acid (E7) (10 mg) as a TFA salt (off-white solid). δH (DMSO-d6, 400 MHz): 1.11 (3H, t), 1.34 (6H, d), 2.88 (4H, m), 3.43 (2H, m), 3.62 (1H, m), 4.29 (4H, m), 4.94 (1H, m), 7.39 (1H, t), 7.51 (3H, m), 8.24 (2H, m), 10.08 (1H, br s), 13.13 (1H, br s). δF (DMSO-d6, 376 MHz): −73.4, −61.3. MS (ES): C26H28F3N3O3S requires 519. found 520.2 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in THF
  3. filtrationfiltered
  4. customThe filtrate was purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-95363475999c40dda5f3edfcf75a6964
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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