188548-67-6

Basic information

• Product Name: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide
• Synonyms: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide
• CAS NO: 188548-67-6
• Molecular Weight: 209.245
• Mol File: 188548-67-6.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide(188548-67-6)
• EPA Substance Registry System: (R)-2-hydroxy-N-methoxy-N-methyl-3-phenylpropanamide(188548-67-6)

Safety Data

• Hazardous Substances Data: 188548-67-6(Hazardous Substances Data)

Upstream product

• 828-01-3 D-phenyllactic acid 
• 673-06-3 D-(R)-phenylalanine 
• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 141694-29-3 N-Methoxy-N-methyl-α-oxobenzenepropanamide 

Downstream Products

• 188548-75-6 5-[(S)-2-Imidazol-1-yl-1,3-diphenyl-prop-(E)-ylideneaminooxy]-pentanoic acid ethyl ester 
• 188548-69-8 5-[(R)-2-Hydroxy-1,3-diphenyl-prop-(E)-ylideneaminooxy]-pentanoic acid ethyl ester 
• 69897-44-5 (R)-2-Hydroxy-1,3-diphenyl-propan-1-one 

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Nucleophilic substitution on α-mesyloxy-O-alkyloximes - I. Enantiospecific synthesis of 2-(imidazol-1-yl) -1,3-diphenylpropan-1-one o-alkyloximes

An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-1-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral α-hydroxyketones 9 were obtained from α-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on α-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on α-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives.