Water → HCID 86659017, compound

HRID 1942721Notes

Reaction equation

HRID 1942721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([C:17]3[C:18]([CH2:31][CH3:32])=[C:19]([CH2:23][N:24]4[CH2:27][CH:26]([C:28]([OH:30])=[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].C1COCC1.O.[CH3:39][C:40]1[CH:41]=[CH:42][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:44][CH:45]=1.O>C(#N)C>[CH3:39][C:40]1[CH:41]=[CH:42][C:43]([S:46]([O-:49])(=[O:48])=[O:47])=[CH:44][CH:45]=1.[C:28]([CH:26]1[CH2:27][NH+:24]([CH2:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:15]3[S:16][C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:10])[CH3:11])=[C:2]([Cl:1])[CH:3]=4)=[N:13][N:14]=3)[C:18]=2[CH2:31][CH3:32])[CH2:25]1)([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

Product 1

HCID 86659017HCID 86659017, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylic acid (50 mg, 0.106 mmol) was added to a mixture of THF (1 mL), water (0.6 mL) and ACN (2 mL), a suspension was obtained to which was added p-TsOH.H2O (24.26 mg, 0.117 mmol). A solution was obtained and stirred for 30 min at rt. Solvent was removed under the reduced pressure and dried in vacuum to give 3-carboxy-1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidin-1-ium 4-methylbenzenesulfonate (65 mg) as pale yellow oil.

Workup

  1. customa suspension was obtained to which
  2. customA solution was obtained
  3. customSolvent was removed under the reduced pressure
  4. customdried in vacuum

Sources & evidence

ORD record
ord-f2ae7e35ff844f659938d846b0bab169
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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