JP2007274963A5 - - Google Patents
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- JP2007274963A5 JP2007274963A5 JP2006105064A JP2006105064A JP2007274963A5 JP 2007274963 A5 JP2007274963 A5 JP 2007274963A5 JP 2006105064 A JP2006105064 A JP 2006105064A JP 2006105064 A JP2006105064 A JP 2006105064A JP 2007274963 A5 JP2007274963 A5 JP 2007274963A5
- Authority
- JP
- Japan
- Prior art keywords
- benzylaminovaleric
- methyl ester
- acid methyl
- acid
- optically active
- 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.)
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- -1 (S) -3-benzylaminovaleric acid Chemical compound 0.000 description 4
- RYDVIDRTLOONEX-GFCCVEGCSA-N methyl (3R)-3-(benzylamino)pentanoate Chemical compound COC(=O)C[C@@H](CC)NCC1=CC=CC=C1 RYDVIDRTLOONEX-GFCCVEGCSA-N 0.000 description 2
- RYDVIDRTLOONEX-UHFFFAOYSA-N methyl 3-(benzylamino)pentanoate Chemical compound COC(=O)CC(CC)NCC1=CC=CC=C1 RYDVIDRTLOONEX-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003287 optical Effects 0.000 description 2
- 229940040461 Lipase Drugs 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241001661345 Moesziomyces antarcticus Species 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 108090001060 lipase Proteins 0.000 description 1
- 102000004882 lipase Human genes 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
実施例１（（Ｓ）−３−ベンジルアミノ吉草酸及び（Ｒ）−３−ベンジルアミノ吉草酸メチルエステルの合成）
水を飽和させたｔ−ブチルメチルエーテル８９０ｍＬに、３−ベンジルアミノ吉草酸メチルエステル（ラセミ体混合物）８９．０ｇ（４０２ｍｍｏｌ）、カンジダ・アンタークティカ（Candida antarctica）由来のリパーゼ８９０ｍｇ（Ｎｏｖｏｚｙｍ ４３５（商品名）；ノボザイム社製）を加え、攪拌しながら３０℃で３４時間反応させた。濾過後、（Ｓ）−３−ベンジルアミノ吉草酸３１．７ｇ（３−ベンジルアミノ吉草酸メチルエステル（ラセミ体混合物）基準の単離収率＝３８．０％）を得た。
（Ｓ）−３−ベンジルアミノ吉草酸は、光学活性カラムを用いた高速液体クロマトグラフィーを使用して光学純度を測定したところ９８．２％ｅｅであった。
（Ｒ）−３−ベンジルアミノ吉草酸メチルエステルを常法により（Ｒ）−３−（Ｎ−ベンゾイル−Ｎ−ベンジル−アミノ）吉草酸メチルエステルに誘導して、光学活性カラムを用いた高速液体クロマトグラフィーを使用して光学純度を測定したところ７７．０％ｅｅであった。
なお、本反応におけるＥ値は２５９であった。
Example 1 (Synthesis of (S) -3-benzylaminovaleric acid and (R) -3-benzylaminovaleric acid methyl ester)
To 890 mL of t-butyl methyl ether saturated with water, 89.0 g (402 mmol) of 3-benzylaminovaleric acid methyl ester (racemic mixture) , 890 mg of lipase derived from Candida antarctica (Novozym 435 ( (Trade name); manufactured by Novozyme) was added and reacted at 30 ° C. for 34 hours with stirring. After filtration, 31.7 g of (S) -3-benzylaminovaleric acid (isolated yield based on 3-benzylaminovaleric acid methyl ester (racemic mixture) = 38.0%) was obtained.
When the optical purity of (S) -3-benzylaminovaleric acid was measured using high performance liquid chromatography using an optically active column, it was 98.2% ee.
(R) -3-Benzylaminovaleric acid methyl ester is converted to (R) -3- (N-benzoyl-N-benzyl-amino) valeric acid methyl ester by a conventional method, and a high-speed liquid using an optically active column The optical purity measured by chromatography was 77.0% ee.
The E value in this reaction was 259.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006105064A JP5088462B2 (en) | 2006-04-06 | 2006-04-06 | Process for producing optically active (R or S) -N-substituted-β-amino acids and optically active (S or R) -N-substituted-β-amino acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006105064A JP5088462B2 (en) | 2006-04-06 | 2006-04-06 | Process for producing optically active (R or S) -N-substituted-β-amino acids and optically active (S or R) -N-substituted-β-amino acid alkyl esters |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012097936A Division JP2012161332A (en) | 2012-04-23 | 2012-04-23 | METHOD FOR PRODUCING OPTICALLY ACTIVE (R OR S)-N-SUBSTITUTED-β-AMINO ACID AND OPTICALLY ACTIVE (S OR R)-N-SUBSTITUTED-β-AMINO ACID ALKYL ESTER |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007274963A JP2007274963A (en) | 2007-10-25 |
| JP2007274963A5 true JP2007274963A5 (en) | 2008-08-28 |
| JP5088462B2 JP5088462B2 (en) | 2012-12-05 |
Family
ID=38677161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006105064A Expired - Fee Related JP5088462B2 (en) | 2006-04-06 | 2006-04-06 | Process for producing optically active (R or S) -N-substituted-β-amino acids and optically active (S or R) -N-substituted-β-amino acid alkyl esters |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5088462B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3819082B2 (en) * | 1996-05-24 | 2006-09-06 | 三菱レイヨン株式会社 | Optically active 3-N-substituted aminoisobutyric acids and salts thereof and process for producing them |
| US7449325B2 (en) * | 2002-04-08 | 2008-11-11 | Ube Industries, Ltd. | Process for enzymatically producing either optically active N-substituted β-amino acids or esters thereof or optically active N-substituted 2-homopipecolic acids or esters thereof |
-
2006
- 2006-04-06 JP JP2006105064A patent/JP5088462B2/en not_active Expired - Fee Related
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