Phenethylamine → 2-[2-(2-Fluorophenyl)-3-(2-phenylethyl)-4-oxo-thiazolidin-5-yl]-acetic acid

HRID 50638

Reaction equation

HRID 50638 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[SH:19][CH:20]([CH2:24][C:25]([OH:27])=[O:26])[C:21](O)=[O:22].C(OC)(OC)OC>CCOC(C)=O>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]1[N:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21](=[O:22])[CH:20]([CH2:24][C:25]([OH:27])=[O:26])[S:19]1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 6268(+-)-Mercaptosuccinic acidHCID 9005Trimethyl orthoformateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 227365532-[2-(2-Fluorophenyl)-3-(2-phenylethyl)-4-oxo-thiazolidin-5-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of phenylethylamine (85 μl), 2-fluorobenzaldehyde (143 μl) and mercaptosuccinic acid (306 mg) and trimethyl orthoformate (0.5 mL) in THP (3 mL) was heated at 80° C. for 4 hrs. The reaction mixture was cooled, diluted with EtOAc (2 mL) and washed twice with 2 ml of 1N HCl. The organic layer was concentrated to give a residue that was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed twice with 2 ml of 1N HCl
  3. concentrationThe organic layer was concentrated
  4. customto give a residue that
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-601b27046db14f1eb07f3a4a77cbdb06
Source dataset
uspto-grants-2004_03
Patent number
US06713477B1

Linked notes

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