Hydrochloric Acid → HCID 86659014, compound

HRID 1942718Notes

Reaction equation

HRID 1942718 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].Cl>C1COCC1.O.C(#N)C>[Cl-: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 2

HCID 313Hydrochloric AcidHCID 584940121-(3-(5-(3-Chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidine-3-carboxylic acid

Product 1

HCID 86659014HCID 86659014, compoundYield 198.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{[3-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-2-ethylphenyl]methyl}-3-azetidinecarboxylic acid (18.95 g) in THF (700 mL), water (190 mL) and acetonitrile (50 mL) was added methanolic hydrogen chloride (44.2 mL, 1.0 M). A clear solution was obtained and stirred for 30 min at rt. The solution was concentrated under the reduced pressure then dried in vacuum at 50° C. to give 3-carboxy-1-(3-(5-(3-chloro-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-ethylbenzyl)azetidin-1-ium chloride (Example 4C, 20.3 g) as white solid. δH (DMSO-d6, 400 MHz): 1.09 (3H, t), 1.35 (6H, d), 2.92 (2H, q), 3.68 (1H, m), 4.26 (4H, m), 4.59 (2H, br. s.), 4.84 (1H, dt), 7.38 (1H, d), 7.47 (1H, m), 7.65 (1H, d), 7.73 (1H, br. s.), 7.96 (1H, dd), 8.10 (1H, d), 11.33 (1H, br. s.), 13.13 (1H, br. s.).

Workup

  1. customA clear solution was obtained
  2. concentrationThe solution was concentrated under the reduced pressure
  3. customthen dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-3b74c65097324359a5d478cc60640497
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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