109010-59-5

Basic information

• Product Name: (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester
• Synonyms: (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester
• CAS NO: 109010-59-5
• Molecular Weight: 393.417
• Mol File: 109010-59-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester(109010-59-5)
• EPA Substance Registry System: (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester(109010-59-5)

Safety Data

• Hazardous Substances Data: 109010-59-5(Hazardous Substances Data)

Upstream product

• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 156386-82-2 trans-γ-3-benzoylprop-2-en-1-ol 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 1005327-17-2 (R)-1-phenyl-2-(2-phenyl-1,3,2-dioxaborolan-4-yl)ethanone 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 244277-48-3 ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate 

Downstream Products

• 133608-98-7 (R)-2-tert-Butoxycarbonyl-3-phenethyl-succinic acid 1-tert-butyl ester 4-ethyl ester 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 
• 109010-61-9 (2S,3'S)-2-(1-tert-butoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester 
• 106860-19-9 (1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate 
• 133609-00-4 (R)-2-Phenethyl-succinic acid 1-ethyl ester 
• 111902-57-9 temocapril 
• 113955-30-9 (S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 113955-31-0 (S)-2-((R)-4-Carboxymethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid 
• 110221-37-9 (S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 113955-29-6 (S)-2-((R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-4,5,6,7-tetrahydro-[1,4]thiazepin-6-ylamino)-4-phenyl-butyric acid ethyl ester 

Relevant articles and documents

Chloramphenicol base chemistry. Part 10: Asymmetric synthesis of α-hydroxy chiral alcohols via intramolecular Michael additions of γ-hydroxy-α, β-unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts

We have developed the chloramphenicol base urea-catalyzed intramolecular Michael addition of γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE inhibitor benazepril hydrochloride.

Ethyl 2,4-dioxo-4-phenylbutyrate: A versatile intermediate for the large-scale preparation of enantiomerically pure α-hydroxy and α-amino acid esters

Starting from ethyl 2,4-dioxo-4-phenylbutyrate, both enantiomers of six enantiomerically pure α-hydroxy and α-amino acid esters (homophenylalanine derivatives) were prepared on >100 g scale. The key step involves a Pt-cinchona catalyzed enantioselective hydrogenation followed by enrichment via crystallization. All derivatives are commercially available.

Note on the synthesis of an optically active ACE inhibitor with amino-oxo-benzazepine-1-alkanoic-acid structure by means of an enantioconvergent crystallization-based resolution

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