KR910002878A - 2-디아조-3-삼치환된 실일옥시-3-부테노에이트의 제조방법 - Google Patents
2-디아조-3-삼치환된 실일옥시-3-부테노에이트의 제조방법 Download PDFInfo
- Publication number
- KR910002878A KR910002878A KR1019900010779A KR900010779A KR910002878A KR 910002878 A KR910002878 A KR 910002878A KR 1019900010779 A KR1019900010779 A KR 1019900010779A KR 900010779 A KR900010779 A KR 900010779A KR 910002878 A KR910002878 A KR 910002878A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- formula
- substituted
- nitrobenzyl
- independently
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 4
- WJHCUMCGWYZKLJ-UHFFFAOYSA-N 2-silyloxybut-3-enoic acid Chemical class C=CC(C(=O)O)O[SiH3] WJHCUMCGWYZKLJ-UHFFFAOYSA-N 0.000 title 1
- -1 silyl halides Chemical class 0.000 claims 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical class OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 claims 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims 1
- 229910052801 chlorine Chemical group 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 일반식(2)의 디아조아세테이트 및 일반식(3)의 삼치환된 실일 할리이드를 디이소프로필 에틸아민, DBU, DBN 또는 트리(C1-C4)알킬아민 및 요오드화 나트룸, 요오드화 칼륨 및 요도드화 세슘으로 이루어진 그룹에서 선택된 염과 반응시킴을 특징으로 하여, 일반식(1)의 2-디아조-3-삼치환된 실일옥시3-부테노에이트 에스테르를 제조하는 방법.상기식에서, R1은, a)C1-6알킬: b)C2-C6알케닐: c)각기 수소, 브롬, 불소, C1-C4알킬, C1-C4알콕시 또는 니트로인 치환체 1 내지 3개에 의해 치환된 페닐: d) 상기 c)의 치환체에 의해 치환된 C1-C4알킬: e)벤즈하이드릴 또는 트리틸이고, R2,R3및 R4는 각기 독립적으로, f)C1-C4알킬, g)각기 수소 또는 C1-C4알킬인 치환제 1 내지 3개에 의해 치환된 페닐, h)-OR5〔여기에서 R5는 상기 f)또는 g)이다〕로 이루어진 그룹에서 선택되며, x는 브롬 또는 염소이다.
- 제1항에 있어서, R1이 페닐 (이것은 수소, 브롬, C1-C4알킬, C1-C4알콕시 또는 니트로에 의해 치환된다)에 의해 치환된 C1-C4알케닐 또는 C1-C4알킬이고, R2, R3및 R4가 각기 독립적으로 C1-C4알킬, 페닐 또는 페녹시인 방법.
- 일반식(2)의 디아조아세테이트를 일반(3)의 삼치환된 실일 클로라이드를 트리( C1-C4알킬)아민인 염기 및 요오드화 칼륨 또는 요오드와 나트륨인 염과 반응시킴을 특징으로 하여, 일반식(1)의 2-디아조-3-삼치환된 실일옥시 3-부테노에이트 에스테르를 제조하는 방법.상기식에서, R1은 알릴, 벤질, 벤즈하이드릴, 신나일, p-프로모벤질, p-메톡시벤질, p-니트로벤질, o-니트로벤질, 2,4,6-트리메틸벤질 또는 트리페닐메틸이고, R2, R3및 R4는 각기 독립적으로, C1-C4알킬이다.
- 제3항에 있어서, R1이 p-메톡시벤질 또는 p-니트로벤질이고 R2, R3및 R4가 각기 독립적으로 메틸, 에틸 및 t-부틸로 이루어진 그룹에서 선택되는 방법.
- 제3항에 있어서, R1이 p-니트로벤질이고 R2, R3및 R4가 각각 메틸이며, 염기는 트리에틸아민이고 염은 요오드화나트륨인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38134489A | 1989-07-18 | 1989-07-18 | |
| US381344 | 1989-07-18 | ||
| US381,344 | 1989-07-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910002878A true KR910002878A (ko) | 1991-02-26 |
| KR0154534B1 KR0154534B1 (ko) | 1998-12-01 |
Family
ID=23504655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900010779A KR0154534B1 (ko) | 1989-07-18 | 1990-07-16 | 2-디아조-3-삼치환된 실릴옥시-3-부테노에이트의 제조방법 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0409331A3 (ko) |
| JP (1) | JPH0395193A (ko) |
| KR (1) | KR0154534B1 (ko) |
| AU (1) | AU625924B2 (ko) |
| CA (1) | CA2021253A1 (ko) |
| FI (1) | FI93363C (ko) |
| IE (1) | IE902601A1 (ko) |
| IL (1) | IL95024A (ko) |
| NO (1) | NO177307C (ko) |
| NZ (1) | NZ234411A (ko) |
| PT (1) | PT94697B (ko) |
| ZA (1) | ZA905595B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR002507A1 (es) * | 1995-06-28 | 1998-03-25 | Merck & Co Inc | Proceso mejorado para sintetizar intermediarios de carbapenem |
| JP2003277390A (ja) * | 2002-03-25 | 2003-10-02 | Takasago Internatl Corp | アゼチジノン化合物の製造方法 |
| EP1670806B9 (en) | 2003-08-28 | 2010-06-02 | Ranbaxy Laboratories Limited | Process for preparation of esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444685A (en) * | 1981-04-27 | 1984-04-24 | Merck & Co., Inc. | Stereospecific synthesis of thienamycin from penicillin |
| US4683296A (en) * | 1983-03-07 | 1987-07-28 | Bristol-Myers Company | Carbapenem intermediates |
| JP2675625B2 (ja) * | 1989-01-12 | 1997-11-12 | 鐘淵化学工業株式会社 | エノールシリルエーテル化合物の製造方法 |
-
1990
- 1990-07-09 NZ NZ234411A patent/NZ234411A/en unknown
- 1990-07-10 IL IL9502490A patent/IL95024A/en not_active IP Right Cessation
- 1990-07-13 EP EP19900201906 patent/EP0409331A3/en not_active Withdrawn
- 1990-07-13 PT PT94697A patent/PT94697B/pt not_active IP Right Cessation
- 1990-07-16 KR KR1019900010779A patent/KR0154534B1/ko not_active IP Right Cessation
- 1990-07-16 CA CA002021253A patent/CA2021253A1/en not_active Abandoned
- 1990-07-17 AU AU59130/90A patent/AU625924B2/en not_active Ceased
- 1990-07-17 NO NO903196A patent/NO177307C/no not_active IP Right Cessation
- 1990-07-17 IE IE260190A patent/IE902601A1/en unknown
- 1990-07-17 ZA ZA905595A patent/ZA905595B/xx unknown
- 1990-07-17 FI FI903604A patent/FI93363C/fi not_active IP Right Cessation
- 1990-07-17 JP JP2187318A patent/JPH0395193A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO903196L (no) | 1991-01-21 |
| PT94697B (pt) | 1997-03-31 |
| NO177307C (no) | 1995-08-23 |
| EP0409331A2 (en) | 1991-01-23 |
| JPH0395193A (ja) | 1991-04-19 |
| FI93363B (fi) | 1994-12-15 |
| AU625924B2 (en) | 1992-07-16 |
| NZ234411A (en) | 1991-05-28 |
| NO903196D0 (no) | 1990-07-17 |
| FI93363C (fi) | 1995-03-27 |
| ZA905595B (en) | 1992-05-27 |
| PT94697A (pt) | 1991-03-20 |
| IL95024A0 (en) | 1991-06-10 |
| CA2021253A1 (en) | 1991-01-19 |
| KR0154534B1 (ko) | 1998-12-01 |
| AU5913090A (en) | 1991-01-24 |
| NO177307B (no) | 1995-05-15 |
| EP0409331A3 (en) | 1991-06-12 |
| IL95024A (en) | 1995-01-24 |
| FI903604A0 (fi) | 1990-07-17 |
| IE902601A1 (en) | 1991-02-27 |
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