CA2219278A1 - Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid - Google Patents
Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acidInfo
- Publication number
- CA2219278A1 CA2219278A1 CA002219278A CA2219278A CA2219278A1 CA 2219278 A1 CA2219278 A1 CA 2219278A1 CA 002219278 A CA002219278 A CA 002219278A CA 2219278 A CA2219278 A CA 2219278A CA 2219278 A1 CA2219278 A1 CA 2219278A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- methylhexanoic acid
- carbamoylmethyl
- aminomethyl
- reacting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title abstract 3
- NPDKTSLVWGFPQG-SSDOTTSWSA-N (3r)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@H](CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-SSDOTTSWSA-N 0.000 abstract 3
- UATSLDZQNXAKMA-UHFFFAOYSA-N 3-(2-methylpropyl)pentanedioic acid Chemical compound CC(C)CC(CC(O)=O)CC(O)=O UATSLDZQNXAKMA-UHFFFAOYSA-N 0.000 abstract 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 alkyl cyanoacetate Chemical compound 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a method of making (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid which comprises condensing isovaleraldehyde with an alkyl cyanoacetate to form a 2-cyano-5-methylhex-2-enoic acid alkyl ester, reacting the 2-cyano-5-methylhex-2-enoic acid alkyl ester with a dialkyl malonate to form 3-isobutylglutaric acid; forming the anhydride of 3-isobutylglutaric acid;
reacting the anhydride with ammonia to form (~)-3-(carbamoylmethyl)-5-methylhexanoic acid' reacting (t)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-.alpha.-phenylethylamine to obtain the (R)-(+)-.alpha.-phenylethylamine salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid;
combining the salt with an acid to obtain (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid' and reacting the (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid with a Hofmann reagent to obtain (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid.
reacting the anhydride with ammonia to form (~)-3-(carbamoylmethyl)-5-methylhexanoic acid' reacting (t)-3-(carbamoylmethyl)-5-methylhexanoic acid with (R)-(+)-.alpha.-phenylethylamine to obtain the (R)-(+)-.alpha.-phenylethylamine salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid;
combining the salt with an acid to obtain (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid' and reacting the (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid with a Hofmann reagent to obtain (S)-(+)-3-(aminomethyl)-5-methylhexanoic acid.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/458,950 US5616793A (en) | 1995-06-02 | 1995-06-02 | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
US458,950 | 1995-06-02 | ||
PCT/US1996/005831 WO1996038405A1 (en) | 1995-06-02 | 1996-04-26 | Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2219278A1 true CA2219278A1 (en) | 1996-12-05 |
CA2219278C CA2219278C (en) | 2006-06-13 |
Family
ID=36587392
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002219278A Expired - Fee Related CA2219278C (en) | 1995-06-02 | 1996-04-26 | Methods of making (s)-3-(aminomethyl)-5-methylhexanoic acid |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2219278C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109761838A (en) * | 2019-02-22 | 2019-05-17 | 浙江华海药业股份有限公司 | A method of preparing pregabalin intermediate and recycling resolving agent |
-
1996
- 1996-04-26 CA CA002219278A patent/CA2219278C/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109761838A (en) * | 2019-02-22 | 2019-05-17 | 浙江华海药业股份有限公司 | A method of preparing pregabalin intermediate and recycling resolving agent |
Also Published As
Publication number | Publication date |
---|---|
CA2219278C (en) | 2006-06-13 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |