87377-66-0

Upstream product

• 87377-65-9 benzyl 5-iodo-3-(2-acetoxyethyl)-4-methylpyrrole-2-carboxylate 
• 66154-72-1 benzyl 3-(β-acetoxyethyl)-4,5-dimethyl-2-pyrrolecarboxylate 
• 62562-72-5 benzyl 3-(benzyloxycarbonylmethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 87377-63-7 ethyl 4-diethylaminomethyl-3-(ethoxycarbonylmethyl)-5-methylpyrrole-2-carboxylate 
• 87377-64-8 5-benzyloxycarbonyl-4-(2-acetoxyethyl)-3-methylpyrrole-2-carboxylic acid 
• 54278-18-1 ethyl 3-(ethoxycarbonylmethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 62562-76-9 benzyl 3-(2-hydroxyethyl)-4,5-dimethylpyrrole-2-carboxylate 
• 74839-03-5 5-ethoxycarbonyl-4-ethoxycarbonylmethyl-2-methylpyrrole-3-carboxylic acid 
• 100-51-6 benzyl alcohol 
• 1738-76-7 glycine benzyl ester p-toluenesulfonic acid salt 
• 51354-16-6 [N-formyl(O-benzyl)]glycinate 
• 21461-49-4 3-acetoxy-1-nitropropane 
• 41995-26-0 benzyl isocyanoacetate 
• 1063682-02-9 Acetic acid 4-acetoxy-1-methyl-2-nitro-butyl ester 

Downstream Products

• 87377-72-8 dibenzyl 3'-(2-chloroethyl)-4-(2-acetoxyethyl)-3,4'-dimethylpyrromethane-5,5'-dicarboxylate 
• 87377-71-7 C₃₁H₃₃ClN₂O₅ 

Relevant academic research and scientific papers

Regioselective synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates from benzyl isocyanoacetate

A general synthesis of 5-unsubstituted benzyl pyrrole-2-carboxylates was developed based on the reaction of β-nitroacetates with benzyl isocyanoacetate. The advantage of this route over other pyrrole syntheses was the regiochemical control of the substitution pattern on the pyrrole ring.

SYNTHESIS OF BILIVERDIN IXγ (PTEROBILIN)

Condensation of a bis(acetoxyethyl)pyrromethane dicarboxylic acid (11d) with a diformylpyrroketone (12b) afforded a bis(acetoxyethyl)-γ-meso-hydroxyporphyrin (13d) which was converted into the related bis(chloroethyl)-γ-benzoyloxyporphyrin (14f).The Zn complex of the latter was transformed by brief treatment with base, followed by chloromethylethyl ether into the zinc bis(chloroethyl)-γ-ethoxymethoxyporphyrin (20b).Dehydrochlorination with potassium t-butoxide in t-butanol, and acid catalysed demetallation and deprotection then afforded the somewhat unstable blue γ-oxyprotoporphyrin dimethyl ester (21).The Fe-complex of the latter readily underwent oxidative ring opening by aerial oxidation in pyridine, and after demetallation gave biliverdin IXγ (pterobilin) dimethyl ester (22).