tert-Butyl (4-oxo-4-phenylbutyl)carbamate → Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate

HRID 270490Notes

Reaction equation

HRID 270490 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([NH:26][NH2:27])=[S:25]>C(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:27][N:26]=[C:24]([C:23]2[CH:28]=[CH:29][CH:30]=[C:21]([F:20])[CH:22]=2)[S:25]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14267858tert-Butyl (4-oxo-4-phenylbutyl)carbamateHCID 552816163-Fluorobenzothiohydrazide

Product 1

HCID 67214060Tert-butyl 3-(5-(3-fluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamateYield 90%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of (4-oxo-4-phenylbutyl)-carbamic acid tert-butyl ester (2.2 g, 8.5 mmol) in ethanol/DCM (30 mL/10 mL) was added 3-fluorothiobenzoic acid hydrazide (Takasugi, J. J.; Buckwalter, B. L. European patent EP 1004241, 2004) (1.2 g, 7.1 mmol) at room temperature. After stirring for 3 days, the reaction mixture was concentrated and purified by flash column chromatography (20:1 Hexanes/EtOAc) to provide the product (2.65 g, 90%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by flash column chromatography (20:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-239f5e2c33274bc597ece4e2e37538c9
Source dataset
uspto-grants-2008_11
Patent number
US07449486B2

Reaction notes

Loading…