WO2001012580A1 - Procede de preparation de 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone - Google Patents

Procede de preparation de 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone Download PDF

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Publication number
WO2001012580A1
WO2001012580A1 PCT/JP2000/005401 JP0005401W WO0112580A1 WO 2001012580 A1 WO2001012580 A1 WO 2001012580A1 JP 0005401 W JP0005401 W JP 0005401W WO 0112580 A1 WO0112580 A1 WO 0112580A1
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WO
WIPO (PCT)
Prior art keywords
methyl
chlorophenyl
oxocyclopentanecarboxylate
dimethyl
ethyl
Prior art date
Application number
PCT/JP2000/005401
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Kazuhiko Sunagawa
Hajime Hoshi
Shigeru Mizusawa
Nobuyuki Kusano
Satoru Kumazawa
Original Assignee
Kureha Kagaku Kogyo Kabushiki Kaisha
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to IL15420700A priority Critical patent/IL154207A0/xx
Priority to PL362899A priority patent/PL203074B1/pl
Priority to CNB008198101A priority patent/CN1196665C/zh
Priority to US10/332,471 priority patent/US7166750B1/en
Priority to HU0300723A priority patent/HUP0300723A3/hu
Priority to BRPI0017310-0A priority patent/BR0017310B1/pt
Priority to EP00951956A priority patent/EP1308432B1/en
Priority to KR1020037001725A priority patent/KR100697737B1/ko
Application filed by Kureha Kagaku Kogyo Kabushiki Kaisha filed Critical Kureha Kagaku Kogyo Kabushiki Kaisha
Priority to CZ20030664A priority patent/CZ303562B6/cs
Priority to DE60031454T priority patent/DE60031454T2/de
Priority to AU2000264750A priority patent/AU2000264750A1/en
Priority to JP2001516881A priority patent/JP4979170B2/ja
Priority to UA2003021098A priority patent/UA73364C2/uk
Publication of WO2001012580A1 publication Critical patent/WO2001012580A1/ja
Priority to IL154207A priority patent/IL154207A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Definitions

  • the present invention relates to a method for producing 5-[(4-chlorophenyl) methyl] -2,2-dimethylcyclopentanone, which is an important intermediate of an agricultural and horticultural fungicide metconazole.
  • JP-A-1-93357 and JP-A-1-31664 describe 5-[(4-chlorophenyl) methyl] -12,2-dimethylcyclopentanone. And converting the carbonyl group of the compound into an epoxy group, followed by azolylation to obtain 5 — [(4-chlorophenyl) methyl] —2,2-dimethyl-1— (1H— It is described that 1,2,4-triazole-1-ylmethyl) cyclopentanol (methconazole) can be derived. As a process for producing this 5-[[(4-chlorophenyl) methyl]]-2,2-dimethylcyclopentene, Japanese Patent Application Laid-Open No. Hei 11-93574 describes the method of the following reaction formula 1. I have.
  • reaction formula 3 the production method of the compound (4) in the reaction formula 2 does not have the power yield described in JP-A-1-93574 as in the following reaction formula 3. Reaction formula 3
  • the present invention has been made in view of the above-mentioned circumstances, and has as its object a simple operation of a high-quality 5- [(4-cloguchifu) which is an important intermediate of the agricultural and horticultural fungicide metconazole.
  • V provides a method for producing high-yield [methyl]]-2,2-dimethylcyclopentanone.
  • a first gist of the present invention is that 1-[(4-chlorophenyl) methyl] -3-methyl-2-methyl 2-oxocyclopentanecarboxylate or 1-[(4-chlorophenyl) methyl 1-[(4-chlorophenyl) methyl] —3,3-dimethyl-methyl 3-ethyl-1-oxocyclopentanecarboxylate treated with sodium hydride and methyl halide To obtain methyl 2-oxocyclopentanecarboxylate or 1-[(4-chlorophenyl) methyl] -3,3-dimethyl-2-ethyl 2-oxocyclopentanecarboxylate and hydrolyze it 5- (4-chlorophenyl) methyl] —2,2-dimethylcyclopentanone.
  • the second gist of the present invention is to (1) react dimethyl adipate or getyl adipate with a metal alkoxide, (2) react with a methyl halide after removing generated alcohol, and (3) After completion of the reaction, it is reacted again with the metal alkoxide, (4) after removing the formed alcohol, and then reacting with (4-phenylphenyl) methyl chloride.
  • the third gist of the present invention is to (1) react dimethyl adipate or getyl adipate with a metal alkoxide, (2) react with a methyl halide after removing generated alcohol, and (3) react After completion, it is reacted with the metal alkoxide again, and (4) after removing the formed alcohol, it is reacted with (4-chlorophenyl) methyl chloride.
  • 1 [(4-chlorophenyl) methyl] —3
  • the present invention relates to a method for producing methyl methyl-2-oxocyclopentanecarboxylate or 1-[(4-chlorophenyl) methyl] -13-methyl-12-oxocyclopentanecarboxylate.
  • a fourth gist of the present invention is to provide 5- (4-chlorophenyl) methyl] -2,2-dimethylcyclopentanone as an intermediate for producing metconazole or an agricultural / horticultural fungicide. Lies in the method used as an intermediate for the production.
  • a fifth gist of the present invention is to provide 1-[(4-chlorophenyl) methyl] -13-methyl-2-methyl oxocyclopentanecarboxylate or 11-[(4-chlorophenyl) methyl] 13— Ethyl methyl-2-oxocyclopentanecarboxylate is converted to 5- (4-chlorophenyl) methyl] —2,2-dimethylcyclopentanone, an intermediate for the production of metconazole.
  • the present invention relates to a method used as an intermediate for producing a body or agricultural / horticultural fungicide.
  • a sixth gist of the present invention is that 1-[(4-cyclophenyl) methyl] -3,3-dimethyl-2-oxocyclopentanecarboxylate or 1-[(4-cyclophenyl) methyl Methyl] —3,3-Dimethyl-2-oxocyclopentaneUsed as an intermediate for the production of ethyl carboxylate, an intermediate for the production of metconazole, or an intermediate for the production of agricultural and horticultural fungicides The way to be.
  • Methyl oxocyclopentanecarboxylate is 1-[(4-chlorophenyl) methyl] —3-methyl-1-2-cyclooxopentanecarboxylate and 1-[(4-chlorophenyl) methyl ] -3,3-Dimethyl-2-ethyl oxocyclopentanecarboxylate is chemically substantially equivalent to that of the present invention.
  • the production of methyl [1- (4-chlorophenyl) methyl] —3—methyl-2-oxooxopentanecarboxylate in a high yield can be carried out by the above-mentioned first to fourth steps. This can be achieved by performing the process continuously without the purification process and by performing the following operations (prepared amounts, reaction conditions, etc.).
  • the reaction of the first step is carried out in a solvent since the product 2-sodium oxocyclopentanecarboxylic acid methyl ester sodium salt is a solid.
  • a solvent to be used an aprotic solvent having a boiling point of 75 ° C. or more is preferable because methanol must be removed by distillation.
  • aromatic compounds such as benzene, toluene, xylene, and benzene
  • ether compounds such as dimethoxetane and dioxane. More preferred solvents include toluene, xylene, and benzene.
  • Dimethyl adipate and metal methoxide are charged into this solvent, and the resulting mixture is heated under normal pressure or reduced pressure, and methanol is distilled off together with the solvent.
  • the reaction temperature is usually 70 to 150 ° C, preferably 80 to 130 ° C. If necessary, add additional solvent.
  • the metal methoxide include sodium methoxide and potassium methoxide, and preferably sodium methoxide.
  • the metal methoxide may be in the form of a powder or a solution in methanol.
  • the amount of metal methoxide to be used is usually 0.9 to 1.0 mol per mol of dimethyl adipate charged. If the amount is less than 0.9 mol, the conversion of dimethyl adipate decreases. If the amount is more than 1.0 mol, it is difficult to remove methanol in the reaction system, and the yield is reduced.
  • the product 2-oxocyclopentanecarboxylic acid methyl ester, sodium salt, precipitates 5 '.
  • aprotic polar solvent examples include DMS0, N-methylpyrrolidone, dimethylimidaridinone, dimethylacetamide, and dimethylformamide.
  • the 2-oxocyclopentanecarboxylic acid methyl ester sodium salt obtained in the first step is reacted with methyl halide.
  • the reaction temperature is usually 50 to 120, more preferably 70 to 100 ° C.
  • Methyl halides include methyl chloride, methyl bromide, and methyl iodide.
  • the amount of methyl halide used is usually 0.9 to 1.1 mol per 1 mol of dimethyl adipate charged in the first step. If the amount is less than 0.9 mol, the reaction is not completed. If it is more than 1.1 mol, there is no noticeable adverse effect on the reaction, but if it is used more than this, there is no advantageous effect. After the reaction is completed, excess methyl halide is removed by distillation, if any. Proceeding to the next step with excess methyl halide remaining will consume the metal methoxide added in the next step and adversely affect the reaction.
  • the reaction product of the second step is charged with metal methoxide, and the resulting mixture is heated under normal pressure or reduced pressure in the same manner as in the first step, and methanol is distilled off together with the solvent.
  • the reaction temperature is usually from 70 to 150 ° C, preferably from 80 to 130 ° C. If necessary, add additional solvent.
  • the metal main Tokishido it forces? Preferable to use the same as the first step.
  • the amount of the metal methoxide to be used is generally 0.9 to 1.0 mol per 1 mol of dimethyl adipate charged in the first step. If it is less than 0.9 mol, the conversion of dimethyl adipate decreases. If the amount is more than 1.0 mol, it becomes difficult to remove methanol from the reaction system, and the yield is reduced.
  • the sodium methyl ester of 3-methyl-12-oxocyclopentanecarboxylic acid obtained in the third step is reacted with (4-chlorophenyl) methyl chloride.
  • the reaction temperature is usually 60 to 150. C, preferably 80 to 130 ° C.
  • the amount of the methyl chloride used is usually 0.9 to 1.0 mol per 1 mol of dimethyl adipate charged in the first step. If the amount is less than 0.9 mol, the product of the third step, 3-methyl-2-oxocyclopentane-potassium sulfonic acid methyl ester sodium salt, remains without being consumed, resulting in a decrease in yield.
  • the solvent used as long as it aprotic solvents do not react with the hydrogenation Natoriumu Ya halogenated alkyl le not particularly limited power?, It can be exemplified the following compounds.
  • Aromatic compounds such as benzene, toluene, xylene, and benzene, ether compounds such as THF, dimethoxetane, and dioxane; dimethylformamide, dimethylacetamide, N-methylpyrrolidone, and dimethylsulfoxide
  • Non-protonic polar compounds may be used alone, or a plurality of them may be used in combination.
  • a mixed solvent of an aromatic compound and an ether compound or an aprotic polar compound is preferred.
  • the amount of sodium hydride used in the fifth step is usually 1 to 0.3 to 1.3 mol, preferably 1 to 1 mol of methyl [(4-chlorophenyl) methyl] -3-methyl-2-oxocyclopentanecarboxylate. Is 1.1 to 1.2 mol. If the amount is less than 1.0 mol, the reaction will not be completed, and the yield will decrease. If the amount is more than 1.3 mol, the post-treatment after the completion of the reaction becomes complicated.
  • methyl halide examples include methyl chloride, methyl bromide, and methyl iodide, and methyl bromide and methyl iodide are preferred.
  • a catalytic amount of sodium iodide or potassium iodide may be added.
  • the amount of methyl halide used is usually from 1.0 to 1.3 moles per mole of 1-[((4-chlorophenyl) methyl) -methyl-3-oxomethyl-2-oxocyclopentanecarboxylate] , Preferably from 1.0 to 1.2 moles. If the amount is less than 1.0 mol, the reaction is not completed and the yield is reduced. If the amount is more than 1.3 mol, the unit consumption of methyl halide is deteriorated.
  • the reaction in the fifth step is a strongly exothermic reaction, which produces hydrogen. So, first add sodium hydride to the solvent, and maintain the reaction temperature to obtain 1-[(4-chlorophenyl) methyl] 13. The method of adding methyl 2-methyl-1-oxocyclopentanecarboxylate and methyl halide is preferred.
  • reaction temperature at this time is usually from 50 ° C to the reflux point, preferably from 80 ° C to the reflux point.
  • reaction When the reaction is performed under basic conditions, the reaction is performed in a system using a lower alcohol or an aromatic hydrocarbon in addition to water.
  • the base include alkali metal bases, preferably sodium hydroxide and hydroxylamine.
  • the reaction temperature at this time is usually 50 ° C to reflux point, preferably 80 ° C to reduction point.
  • a 2-liter 4-neck flask was charged with 1 liter of toluene as a solvent, 174.2 g of dimethyl adipate, 189.1 lg of 28% sodium methylate, and 15 g of DMF. Then, the mixture was heated under normal pressure while stirring under nitrogen, and methanol / toluene was distilled off. On the way,
  • a 1-liter four-necked flask was charged with 44.1 g of 60% sodium hydride, and paraffin was removed by decanting with toluene. To this, 100 ml of toluene, 2 Om 1 of dimethoxetane and 1 g of sodium iodide were added. The reactor was fitted with a dry ice condenser, immersed in a bath at 80 ° C, and obtained from Example 1 with [1- (4-chlorophenyl) methyl] —3-methyl-1-oxocyclopentane. 277.7 g of methyl carboxylate and 100 g of methyl bromide were slowly added dropwise.
  • Example 1 When the same operation as in Example 1 was performed except that the same molar number of powdered sodium methylate was used instead of 28% sodium methylate, the same result as in Example 1 was obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2000/005401 1999-08-13 2000-08-11 Procede de preparation de 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone WO2001012580A1 (fr)

Priority Applications (14)

Application Number Priority Date Filing Date Title
EP00951956A EP1308432B1 (en) 2000-08-11 2000-08-11 Process for the preparation of 5- (4-chlorophenyl)-methyl|-2,2-dimethylcyclopentanone
CNB008198101A CN1196665C (zh) 2000-08-11 2000-08-11 5－[(4－氯苯基)甲基]－2,2－二甲基环戊酮的制备方法
US10/332,471 US7166750B1 (en) 2000-08-11 2000-08-11 Process for the preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone
HU0300723A HUP0300723A3 (en) 1999-08-13 2000-08-11 Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcylopentanone
BRPI0017310-0A BR0017310B1 (pt) 1999-08-13 2000-08-11 processo para produzir 5-[(4-clorofenil)metil]-2,2-dimetilciclopentanona.
KR1020037001725A KR100697737B1 (ko) 2000-08-11 2000-08-11 5-[(4-클로로페닐)메틸]-2,2-디메틸시클로펜탄온의 제조방법
CZ20030664A CZ303562B6 (cs) 2000-08-11 2000-08-11 Zpusob výroby 5-[(4-chlorfenyl)methyl]-2,2-dimethylcyklopentanonu
IL15420700A IL154207A0 (en) 2000-08-11 2000-08-11 Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone
PL362899A PL203074B1 (pl) 1999-08-13 2000-08-11 Sposób wytwarzania 5-[(4-chlorofenylo) metylo]- 2,2-dimetylo-1-(1H-1,2,4-triazol-1-ylometylo) cyklopentanolu (Metkonazolu)
DE60031454T DE60031454T2 (de) 2000-08-11 2000-08-11 Verfahren zur herstellung von 5-(4-chlorophenyl)-methyl-2,2-dimethylcyclopentanon
AU2000264750A AU2000264750A1 (en) 1999-08-13 2000-08-11 Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone
JP2001516881A JP4979170B2 (ja) 1999-08-13 2000-08-11 ５−［（４−クロロフェニル）メチル］−２，２−ジメチルシクロペンタノンの製造方法
UA2003021098A UA73364C2 (uk) 1999-08-13 2000-11-08 Спосіб одержання 5-[(4-хлорфеніл)метил]-2,2-диметилциклопентанону та спосіб одержання проміжних сполук (варіанти)
IL154207A IL154207A (en) 1999-08-13 2003-01-30 Process for the preparation of 5 - [(4 - chlorophenyl) - methyl] - 2, 2 - dimethylcyclopentanone

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/264292 1999-08-13
JP26429299 1999-08-13

Publications (1)

Publication Number Publication Date
WO2001012580A1 true WO2001012580A1 (fr) 2001-02-22

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PCT/JP2000/005401 WO2001012580A1 (fr) 1999-08-13 2000-08-11 Procede de preparation de 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone

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JP (1) JP4979170B2 (enrdf_load_stackoverflow)
AR (1) AR025233A1 (enrdf_load_stackoverflow)
AU (1) AU2000264750A1 (enrdf_load_stackoverflow)
BR (1) BR0017310B1 (enrdf_load_stackoverflow)
HU (1) HUP0300723A3 (enrdf_load_stackoverflow)
IL (1) IL154207A (enrdf_load_stackoverflow)
IN (1) IN2005DE05932A (enrdf_load_stackoverflow)
PH (1) PH12000002167B1 (enrdf_load_stackoverflow)
PL (1) PL203074B1 (enrdf_load_stackoverflow)
TW (1) TW591012B (enrdf_load_stackoverflow)
UA (1) UA73364C2 (enrdf_load_stackoverflow)
WO (1) WO2001012580A1 (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012169468A1 (ja) 2011-06-07 2012-12-13 株式会社クレハ シクロペンタノン化合物の製造方法、および中間体化合物
WO2015075981A1 (ja) * 2013-11-22 2015-05-28 株式会社クレハ カルボニル化合物の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0267778A2 (en) * 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
EP0413448A1 (en) * 1989-08-15 1991-02-20 Kureha Kagaku Kogyo Kabushiki Kaisha An Azole-substituted cycloalkanol derivative, a process to produce the same and a use of the derivative as an agricultural and horticultural fungicide
EP0537909A1 (en) * 1991-09-18 1993-04-21 Kureha Chemical Industry Co., Ltd. 3-(Unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivatives, and their preparation and use
EP0731083A1 (en) * 1995-03-10 1996-09-11 Kureha Kagaku Kogyo Kabushiki Kaisha Process for the producing of alkylcyclopentanone derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0267778A2 (en) * 1986-11-10 1988-05-18 Kureha Kagaku Kogyo Kabushiki Kaisha Azole derivatives useful in controlling plant diseases and regulating plant growth
EP0413448A1 (en) * 1989-08-15 1991-02-20 Kureha Kagaku Kogyo Kabushiki Kaisha An Azole-substituted cycloalkanol derivative, a process to produce the same and a use of the derivative as an agricultural and horticultural fungicide
EP0537909A1 (en) * 1991-09-18 1993-04-21 Kureha Chemical Industry Co., Ltd. 3-(Unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivatives, and their preparation and use
EP0731083A1 (en) * 1995-03-10 1996-09-11 Kureha Kagaku Kogyo Kabushiki Kaisha Process for the producing of alkylcyclopentanone derivatives

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012169468A1 (ja) 2011-06-07 2012-12-13 株式会社クレハ シクロペンタノン化合物の製造方法、および中間体化合物
JPWO2012169468A1 (ja) * 2011-06-07 2015-02-23 株式会社クレハ シクロペンタノン化合物の製造方法、および中間体化合物
US8975434B2 (en) 2011-06-07 2015-03-10 Kureha Corporation Method for producing cyclopentanone compound, and intermediate compound
WO2015075981A1 (ja) * 2013-11-22 2015-05-28 株式会社クレハ カルボニル化合物の製造方法

Also Published As

Publication number Publication date
JPWO0112580A1 (en) 2003-03-11
JP4979170B2 (ja) 2012-07-18
PL203074B1 (pl) 2009-08-31
PH12000002167B1 (en) 2008-10-28
BR0017310A (pt) 2003-07-08
IN2005DE05932A (enrdf_load_stackoverflow) 2008-05-09
HUP0300723A3 (en) 2006-06-28
HUP0300723A2 (hu) 2003-09-29
PL362899A1 (en) 2004-11-02
BR0017310B1 (pt) 2011-10-04
TW591012B (en) 2004-06-11
AR025233A1 (es) 2002-11-13
UA73364C2 (uk) 2005-07-15
IL154207A (en) 2008-12-29
AU2000264750A1 (en) 2001-03-13

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