JP4271658B2 - 固相結合ctc樹脂のリサイクル方法 - Google Patents
固相結合ctc樹脂のリサイクル方法 Download PDFInfo
- Publication number
- JP4271658B2 JP4271658B2 JP2004561282A JP2004561282A JP4271658B2 JP 4271658 B2 JP4271658 B2 JP 4271658B2 JP 2004561282 A JP2004561282 A JP 2004561282A JP 2004561282 A JP2004561282 A JP 2004561282A JP 4271658 B2 JP4271658 B2 JP 4271658B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- solid phase
- ctc resin
- alkyl
- organic solvent
- 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.)
- Expired - Lifetime
Links
- 239000011347 resin Substances 0.000 title claims abstract description 37
- 229920005989 resin Polymers 0.000 title claims abstract description 37
- 239000007790 solid phase Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000004064 recycling Methods 0.000 title abstract description 9
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- -1 2-chlorotrityl Chemical group 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 11
- 239000012320 chlorinating reagent Substances 0.000 abstract description 8
- 238000010647 peptide synthesis reaction Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007030 peptide scission Effects 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- RESFKJVKDJYYDQ-UHFFFAOYSA-N trityl 2,2,2-trifluoroacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C(F)(F)F)C1=CC=CC=C1 RESFKJVKDJYYDQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/02—Recovery or working-up of waste materials of solvents, plasticisers or unreacted monomers
Description
の固相結合塩化2−クロロトリチル(2−CTC樹脂)の製造方法であって、塩素化剤と有機溶媒の存在下における式II:
の固相結合2−クロロトリチルの反応を含む、製造方法を記述する。
ガラスフリットボトムを有する二重壁ジャケット反応器において、5gの純粋な「使用済み樹脂」(式II)を、場合により有機溶媒中での前処理(表1)と溶媒の吸引の後、特定の反応温度(T:表1)で、特定の反応時間(t:表1)、溶解された塩素化剤(表1)を有する有機溶媒(表1)中でゆっくりと攪拌した。反応溶媒のパーコレーションと吸引が完結した後、残存樹脂を反応溶媒で洗浄し、ヘキサンで処理し、真空下、35℃で乾燥した。リサイクルされた2−CTC樹脂(式I)の活性塩化物の含量(表1)を測定し[6]、元素分析によるその窒素含量は、検出限界以下であった。未使用の2−CTC樹脂(式I)は、使用前活性塩化物含量:〜1.27mol/kgを有していた。「使用済み樹脂」(式II)は、使用前活性塩化物[6]を全く有さず、RがOC1-4アルキルである式IIの化合物の含量は、5%未満で、0%より多く、窒素含量は、0.2%未満で、0%より多かった。
Claims (6)
- 有機溶媒が、トルエン、クロロベンゼン、CH2Cl2、DMSO、NMP、DMF、アルキルエーテル、DME、ジグリム、THFまたはジオキサンである、請求項1記載の方法。
- nが、以下の意味:0.9≧n≧0.5を有する、請求項1または2記載の方法。
- 反応温度が、0〜110℃の間である、請求項1〜3のいずれか一項記載の方法。
- ジオキサン中のHCl含量が、0を超え40g/100mlまでである、請求項1〜4のいずれか一項記載の方法。
- 反応時間が、6〜96時間である、請求項1〜5のいずれか一項記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02028744 | 2002-12-20 | ||
PCT/EP2003/014111 WO2004056883A2 (en) | 2002-12-20 | 2003-12-12 | Process for the recycling of solid phase bonded ctc-resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006510768A JP2006510768A (ja) | 2006-03-30 |
JP4271658B2 true JP4271658B2 (ja) | 2009-06-03 |
Family
ID=32668735
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004561282A Expired - Lifetime JP4271658B2 (ja) | 2002-12-20 | 2003-12-12 | 固相結合ctc樹脂のリサイクル方法 |
Country Status (14)
Country | Link |
---|---|
US (1) | US7351771B2 (ja) |
EP (1) | EP1578812B1 (ja) |
JP (1) | JP4271658B2 (ja) |
KR (1) | KR100613945B1 (ja) |
CN (1) | CN100491414C (ja) |
AT (1) | ATE328909T1 (ja) |
AU (1) | AU2003293854A1 (ja) |
CA (1) | CA2506533C (ja) |
DE (1) | DE60305976T2 (ja) |
DK (1) | DK1578812T3 (ja) |
ES (1) | ES2264540T3 (ja) |
IL (1) | IL168684A (ja) |
MX (1) | MXPA05006436A (ja) |
WO (1) | WO2004056883A2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE602005023429D1 (de) | 2004-10-19 | 2010-10-21 | Lonza Ag | Verfahren zur festphasen-peptidsynthese |
CN113248352A (zh) * | 2021-05-18 | 2021-08-13 | 湖南华腾制药有限公司 | 一种固相合成七甘醇单甲醚的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2725368A (en) * | 1952-12-09 | 1955-11-29 | Eastman Kodak Co | Preparation of polyvinylbenzene sulfonyl chlorides and derivatives thereof |
US5198531A (en) * | 1991-06-14 | 1993-03-30 | Research Diagnostic Antibodies | Polymeric resin for peptide synthesis |
DE4306839A1 (de) * | 1993-03-05 | 1994-09-08 | Bayer Ernst Prof Dr | Tritylgruppe enthaltendes Festphasensystem, Verfahren zu seiner Herstellung und seine Verwendung in Festphasenreaktionen |
WO2001085758A2 (de) * | 2000-05-12 | 2001-11-15 | Lonza Ag | Verfahren zur herstellung von polymergebundenem 2-chlortritylchlorid |
-
2003
- 2003-12-12 KR KR1020057011270A patent/KR100613945B1/ko not_active IP Right Cessation
- 2003-12-12 ES ES03789239T patent/ES2264540T3/es not_active Expired - Lifetime
- 2003-12-12 AU AU2003293854A patent/AU2003293854A1/en not_active Abandoned
- 2003-12-12 CN CNB2003801057685A patent/CN100491414C/zh not_active Expired - Fee Related
- 2003-12-12 EP EP03789239A patent/EP1578812B1/en not_active Expired - Lifetime
- 2003-12-12 WO PCT/EP2003/014111 patent/WO2004056883A2/en active IP Right Grant
- 2003-12-12 MX MXPA05006436A patent/MXPA05006436A/es active IP Right Grant
- 2003-12-12 CA CA002506533A patent/CA2506533C/en not_active Expired - Fee Related
- 2003-12-12 DK DK03789239T patent/DK1578812T3/da active
- 2003-12-12 JP JP2004561282A patent/JP4271658B2/ja not_active Expired - Lifetime
- 2003-12-12 DE DE60305976T patent/DE60305976T2/de not_active Expired - Lifetime
- 2003-12-12 AT AT03789239T patent/ATE328909T1/de not_active IP Right Cessation
- 2003-12-18 US US10/740,207 patent/US7351771B2/en not_active Expired - Fee Related
-
2005
- 2005-05-19 IL IL168684A patent/IL168684A/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP2006510768A (ja) | 2006-03-30 |
US7351771B2 (en) | 2008-04-01 |
WO2004056883A3 (en) | 2004-08-05 |
EP1578812B1 (en) | 2006-06-07 |
CA2506533A1 (en) | 2004-07-08 |
KR20050089054A (ko) | 2005-09-07 |
KR100613945B1 (ko) | 2006-08-22 |
IL168684A (en) | 2008-11-26 |
DE60305976D1 (de) | 2006-07-20 |
ES2264540T3 (es) | 2007-01-01 |
US20040147717A1 (en) | 2004-07-29 |
MXPA05006436A (es) | 2005-08-19 |
DE60305976T2 (de) | 2006-11-16 |
AU2003293854A1 (en) | 2004-07-14 |
CA2506533C (en) | 2009-05-26 |
EP1578812A2 (en) | 2005-09-28 |
ATE328909T1 (de) | 2006-06-15 |
WO2004056883A2 (en) | 2004-07-08 |
DK1578812T3 (da) | 2006-08-14 |
CN1726232A (zh) | 2006-01-25 |
CN100491414C (zh) | 2009-05-27 |
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