Sodium Hydroxide → 5-(2-Azidopropyl)thiophene-2-carboxylic acid
Reaction equation
C[C:2]([C:4]1[S:5][C:6]([CH2:9][CH:10]([N:12]=[N+:13]=[N-:14])[CH3:11])=[CH:7][CH:8]=1)=[O:3].BrBr.[OH-:17].[Na+]>>[N:12]([CH:10]([CH3:11])[CH2:9][C:6]1[S:5][C:4]([C:2]([OH:3])=[O:17])=[CH:8][CH:7]=1)=[N+:13]=[N-:14]Participants
Procedure
For the preparation of the amine starting material of Example 10f, α-methyl-2-thiophenethanol, acetyl chloride and aluminum chloride were reacted in methylene chloride to give (RS)-2-(5-acetyl-2-thienyl)-1-methylethyl acetate. The resulting acetate was saponified with sodium hydroxide in methanol to give 5-[(RS)-2-hydroxypropyl]-2-thienyl methyl ketone which was subsequently reacted with p-toluenesulfonyl chloride to give (RS)-2-(5-acetyl-2-thienyl)-1-methylethyl-p-toluenesulfonate, m.p. 101°-103°. With sodium azide in dimethylsulfoxide there was obtained therefrom 5-[(RS)-2-azidopropyl]-2-thienyl methyl ketone which was oxidized with bromine in sodium hydroxide solution to give 5-[(RS)-2-azidopropyl]-2-thiophenecarboxylic acid. With thionyl chloride, there was obtained therefrom the corresponding acid chloride and from this there was prepared with ammonia 5-[(RS)-2-azidopropyl]-2-thiophenecarboxamide, m.p. 79°-80° C., from diethyl ether. Treatment with triphenylphosphine and hydrolysis gave 5-[(RS)-2-aminopropyl]-2-thiophenecarboxamide, m.p. 91°-92° from acetonitrile.
Sources & evidence
- ORD record
- ord-fb97398ef68c41dea582f793a008c918
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166218
Reaction notes
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