Sulfuric Acid → HCID 86659015, compound

HRID 1942719Notes

Reaction equation

HRID 1942719 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]([CH:28]=[CH:29][CH:30]=3)[CH2:20][N:21]3[CH2:24][CH:23]([C:25]([OH:27])=[O:26])[CH2:22]3)=[N:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[OH:33][S:34]([OH:37])(=[O:36])=[O:35]>C1COCC1>[S:34]([O-:37])([OH:36])(=[O:35])=[O:33].[C:25]([CH:23]1[CH2:24][NH+:21]([CH2:20][C:19]2[CH:28]=[CH:29][CH:30]=[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])[CH2:22]1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

Product 1

HCID 86659015HCID 86659015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid (100 mg, 0.212 mmol) in THF (2 mL) was added H2SO4 (0.286 mL, 4%, aq. solution). The mixture became clear and stirred for 30 min at rt. The solution was concentrated 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 hydrogensulfate (123 mg) as pale yellow crystalline solid.

Workup

  1. concentrationThe solution was concentrated under the reduced pressure
  2. customdried in vacuum

Sources & evidence

ORD record
ord-e8f65ed5e6264f8eaec63a42f7a6043e
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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