99481-03-5

Upstream product

• 67-56-1 methanol 
• 81720-89-0 (5-acetyl-2-hydroxyphenyl)acetic acid 
• 27798-60-3 methyl 2-(2-methoxyphenyl)acetate 
• 75-36-5 acetyl chloride 
• 99-93-4 4-Hydroxyacetophenone 
• 65236-06-8 5-acetyl-2-hydroxyphenylacetonitrile 
• 24085-05-0 1-(3-chloromethyl-4-hydroxyphenyl)ethanone 

Downstream Products

• 196195-38-7 methyl (5-acetyl-2-benzyloxyphenyl)acetate 
• 371783-91-4 2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-tert-butyldimethylsilyloxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide 
• 371783-92-5 2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-hydroxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide 
• 371783-90-3 (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane 
• 371783-86-7 methyl (2-benzyloxy-5-bromoacetylphenyl)acetate 
• 371783-87-8 (1R)-1-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-bromoethan-1-ol 

Relevant academic research and scientific papers

The practical synthesis of a uterine relaxant, Bis( 2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl) -phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)

The synthetic route for a uterine relaxant, bis(2-{[ (2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3- (2-hydroxyethyl)-phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-y1]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Bromohydrin 14 was obtained by the asymmetric borane reduction of the prochiral phenacyl bromide 13 using a catalyst prepared from aluminum triethoxide and a chiral amino alcohol. The other optically active component 24 was prepared from (S)-AMT.

Novel arylacetic acid derivatives

A compound having a potentially inhibitory effect on 15-hydroxy-prostaglandin dehydrognase (PGDH) and having the formula STR1 in which R1 and R2 are hydrogen or lower alkyl; R3 is hydrogen, lower alkyl or substituted or unsubstituted phenyl; R4, R5, and R6 are hydrogen, halogen, lower alkyl, lower alkoxy, cyano, carboxy or nitro; at least one of the groups R4 to R6 being hydrogen; R7 to R11 are hydrogen, halogen, cyano, lower alkyl, trifluoromethyl, lower alkoxy, hydroxy, lower acyl, lower alkoxycarbonyl, N,N,-diloweralkyl-aminocarbonyl or N,N-loweralkylene-aminocarbonyl; and R8 and R10 may in addition be carboxy; at least two of R7 to R11 always being hydrogen; and --A-- is --CO--, --CH2 --CO--, --CH=CH--, --CH=CH--CO-- or corresponding groups in which a hydrogen atom is replaced by a lower alkyl group. The invention comprises also lactones of those compounds in which R1 is hydrogen, and salts of those compounds which contain at least one carboxy group.