Benzyl Alcohol → HCID 13739162, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH:5](Br)[CH2:6][CH3:7])[CH3:2].[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:9])[CH:5]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][CH3:7])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
As per scheme-12, ethyl-2-bromobutyrate (12-a) is reacted with benzyl alcohol in presence of potassium hydroxide in DMF at 25° C. to 35° C. up to 3 hr to provide ethyl-2-benzyloxybutyrate (12-b). Compound 12-b is treated with hydrazine hydrate in ethanol at reflux temperature to provide corresponding acid hydrazide compound 12-c. The compound 12-c is treated with 2-picolinic acid in the presence of dehydrating agent EDC along with HOBt and N-methyl morpholine in DMF at a temperature 0° C. to 30° C. for 1 hr to provide uncyclized compound 12-d. The compound 12-d is further treated with Lawesson's reagent in tetrahydrofuran at a reflux temperature for 4 hr to provide corresponding pyridinyl-1,3,4-thiadiazolyl compound 12-e. The compound 12-e is stirred with borontribromide in dichloromethane at a temperature ranging from 0° C. to 5° C. for 1 hr followed by at 35° C. for overnight, to provide corresponding pyridinyl-1,3,4-thadiazolyl propanol compound 12-f. The compound 12-f is treated with p-nitrophenylsulfonyl chloride in the presence triethylamine in a dichloromethane at a temperature ranging from 0° C. to 15° C. to provide corresponding p-nitrophenyl sulfonic acid ester compound 12-g.
Sources & evidence
- ORD record
- ord-ab36c9d086dd4782b14d6e650ea5b113
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09175031B2
Reaction notes
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