C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 327/34 (2006.01) C07C 235/34 (2006.01) C07C 275/42 (2006.01) C07C 303/28 (2006.01) C07C 309/63 (2006.01) C07C 323/59 (2006.01) C07C 327/32 (2006.01) C07D 207/16 (2006.01) C07D 209/20 (2006.01) C07D 233/64 (2006.01) C07C 309/66 (2006.01) C07C 309/73 (2006.01)
Patent
CA 2262224
An optically active N-[2(acetylthiomethyl)-1-oxo-3- phenylpropyl]-amino acid ester of formula (I): (see fig. I) wherein R1 represents a hydrogen atom, an amino acid side chain or a protected amino acid side chain; R2 represents a linear or branched C1 to C18 alkyl group or an unsubstituted or substituted benzyl group; and represents an optically active carbon atom, is produced by a method comprising the steps of: a) reacting optically active 2-hydroxymethyl-3phenylpropionic acid of formula (II): (see fig. II)~ with an amino acid ester or a salt thereof for conversion into optically active N-[2-hydroxymethyl-1-oxo-3- phenylpropyl]-amino acid ester of formula (III): (see fig. III) wherein R1 and R2 have the aforesaid meanings and * represents an optically active carbon atom; b) activating the hydroxyl group of the hydroxymethyl group at 2-position of the compound of formula (III) for conversion into optically active N-acylamino acid ester having the general formula (IV): (see fig. IV) wherein R1 and R2 have the aforesaid meanings, X represents a chloride, bromide or iodide atom, a linear, branched or cyclic, unsubstituted or substituted C1 - C6 alkylsulfonyloxy group, or a C6 - C18 arylsulfonyloxy group and * represents an optically active carbon atom, and c) reacting the compound of formula (IV) with a thioacetate salt or thioacetic acid in the presence of a base. The method of the invention is particularly useful for producing optically active N-[2-(acetylthiomethyl)-1- oxo-3-phenylpropyl]-glycine benzyl ester.
Hamada Takayuki
Izawa Kunisuke
Suzuki Takayuki
Ajinomoto Co. Inc.
Ogilvy Renault Llp/s.e.n.c.r.l.,s.r.l.
LandOfFree
Method for producing optically active phenylpropionic acid... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method for producing optically active phenylpropionic acid..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for producing optically active phenylpropionic acid... will most certainly appreciate the feedback.
Profile ID: LFCA-PAI-O-1759521