JP2001011060A5 - - Google Patents
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- Publication number
- JP2001011060A5 JP2001011060A5 JP1999181933A JP18193399A JP2001011060A5 JP 2001011060 A5 JP2001011060 A5 JP 2001011060A5 JP 1999181933 A JP1999181933 A JP 1999181933A JP 18193399 A JP18193399 A JP 18193399A JP 2001011060 A5 JP2001011060 A5 JP 2001011060A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- mol
- dimethylformamide
- nitrobenzoic acid
- chloride
- 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.)
- Pending
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KPJXEWJRJKEOCD-UHFFFAOYSA-N 2-Methoxy-4-nitrobenzoic acid Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(O)=O KPJXEWJRJKEOCD-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OCRMTSZMJWPEEY-UHFFFAOYSA-N ethyl 5-(2-methoxy-4-nitrophenyl)-1,3-oxazole-4-carboxylate Chemical compound N1=COC(C=2C(=CC(=CC=2)[N+]([O-])=O)OC)=C1C(=O)OCC OCRMTSZMJWPEEY-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- DJDAPLBWGIXUAG-UHFFFAOYSA-N 2-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(Cl)=O DJDAPLBWGIXUAG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
【００１２】
【実施例】
以下、本発明を実例を挙げて詳述する。「％」は重量基準である。
実施例１
５−（２−メトキシ−４−ニトロフェニル）−４−カルボエトキシオキサゾールの合成
２−メトキシ−４−ニトロ安息香酸１７．７ｇ（０．０９モル）をＮ，Ｎ−ジメチルホルムアミド８０ｍｌに溶解し、チオニルクロライド１１．９ｇ（０．０９モル）を１時間かけて滴下し２−メトキシ−４−ニトロ安息香酸クロライドを合成した。これとは別にＮ，Ｎ−ジメチルホルムアミド５０ｍｌにトリエチルアミン３０．４ｇ（０．３モル）、イソシアノ酢酸エチル１１．３ｇ（０．１モル）を溶解し０℃に保持しながら、これに先の酸クロライドのＮ，Ｎ−ジメチルホルムアミド溶液を滴下し４時間反応した。
反応終了後、反応生成液を瀘過し瀘液を濃縮した。これをシリカゲルカラムクロマトグラフィーにより精製し、５−（２−メトキシ−４−ニトロフェニル）−４−カルボエトキシオキサゾール１７．２ｇ（０．０５９モル）を得た。２−メトキシ−４−ニトロ安息香酸に対して６５．３％の収率であった。
[0012]
【Example】
Hereinafter, the present invention will be described in detail with reference to examples. “%” Is based on weight.
Example 1
Synthesis of 5- (2-methoxy-4-nitrophenyl) -4-carbethoxyoxazole 17.7 g (0.09 mol) of 2-methoxy-4-nitrobenzoic acid was dissolved in 80 ml of N, N-dimethylformamide, 11.9 g (0.09 mol) of thionyl chloride was added dropwise over 1 hour to synthesize 2-methoxy-4-nitrobenzoic acid chloride. Separately, 30.4 g (0.3 mol) of triethylamine and 11.3 g (0.1 mol) of ethyl isocyanoacetate are dissolved in 50 ml of N, N-dimethylformamide, and while maintaining the temperature at 0.degree. An N, N-dimethylformamide solution of chloride was added dropwise and reacted for 4 hours.
After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated. This was purified by silica gel column chromatography to obtain 5- (2-methoxy-4-nitrophenyl) -4-carboethoxy-oxazole 17.2 g (0. 0 59 mole). The yield was 65.3% based on 2-methoxy-4-nitrobenzoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11181933A JP2001011060A (en) | 1999-06-28 | 1999-06-28 | Novel oxazole and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11181933A JP2001011060A (en) | 1999-06-28 | 1999-06-28 | Novel oxazole and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001011060A JP2001011060A (en) | 2001-01-16 |
| JP2001011060A5 true JP2001011060A5 (en) | 2006-07-06 |
Family
ID=16109442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11181933A Pending JP2001011060A (en) | 1999-06-28 | 1999-06-28 | Novel oxazole and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001011060A (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0774213B2 (en) * | 1986-12-11 | 1995-08-09 | 第一製薬株式会社 | 5- (4-pyridyl) oxazole-4-carboxylic acid or ester thereof |
| JP3065336B2 (en) * | 1990-09-21 | 2000-07-17 | 日本合成化学工業株式会社 | Method for producing 5-substituted oxazole |
| AU6709796A (en) * | 1995-08-30 | 1997-03-19 | Takara Shuzo Co., Ltd. | Immunologically tolerant vertebrate and use of the same |
| CN1116288C (en) * | 1996-04-23 | 2003-07-30 | 沃泰克斯药物股份有限公司 | Urea derivatives as inhibitors of IMPDH enzyme |
| ATE244717T1 (en) * | 1997-03-14 | 2003-07-15 | Vertex Pharma | IMPDH ENZYME INHIBITORS |
-
1999
- 1999-06-28 JP JP11181933A patent/JP2001011060A/en active Pending
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