Sodium Azide → HCID 86740752, compound

HRID 973749Notes

Reaction equation

HRID 973749 reaction equation
[CH3:1]/[C:2](/[C:9]1[S:10][C:11]([CH2:14][CH:15](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:16])=[CH:12][CH:13]=1)=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O>[N:28]([CH:15]([CH3:16])[CH2:14][C:11]1[S:10][C:9](/[C:2](/[CH3:1])=[CH:3]/[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:13][CH:12]=1)=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86740753HCID 86740753, compound

Product 1

HCID 86740752HCID 86740752, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

For the preparation of the amine starting material of Examples 6 and 10g, 5-[(RS)-2-hydroxypropyl]-2-thienyl methyl ketone and triethyl phosphonoacetate were reacted in ethanol in the presence of sodium ethylate to give ethyl (E)-5-[(RS)-2-hydroxypropyl]-β-methyl-2-thiopheneacrylate. With p-toluenesulfonyl chloride, there was obtained therefrom ethyl (E)-β-methyl-5-[(RS)-2-[(p-toluenesulphonyl)oxy]propyl]-2-thiopheneacrylate (m.p. 121°, from methylene chloride-alcohol. Reaction with sodium azide in dimethylsulfoxide gave ethyl (E)-5-[(RS)--2-azido-propyl]-β-methyl-2-thiopheneacrylate. Reduction with triphenylphosphine and hydrolysis yielded ethyl (E)-5-[(RS)-2-aminopropyl]-β-methyl-2-thiopheneacrylate, ε320 =17970.

Sources & evidence

ORD record
ord-457c1d0272cd4f20878b5338a1b7f3b9
Source dataset
uspto-grants-1991_11
Patent number
US05064863

Reaction notes

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