JPS5838291A - Preparation of 3-cephem derivative - Google Patents

Abstract

NEW MATERIAL:The compound of formulaI(R<1> is acyl). EXAMPLE:7beta-( 2-Thienylacetamido )-9,11-dioxothieno[ 4,3,C ]-3-cephem. USE:A gynthetic intermediate of a compound having effective antibacterial activity against Gram-positive and Gram-negative bacteria. PROCESS:The compound of formulaIcan be prepared in high yield by oxidizing the compound of formula II with >=1mol equivalent, based on the compound of formulaI, of an oxidizing agent (e.g. chromic acid, manganese dioxide, etc.) in an inert solvent such as THF. The compound of formula II used as a starting material is obtained by halogenating the compound of formula III in a solvent such as chloroform, and hydrolyzing the resultant compound of formula IV (X is halogen) in water or in a mixture of water and an organic solvent (e.g. DMF).

Description

[Detailed Description of the Invention] This Jiil! is a compound represented by the general formula [wherein B1 represents an AV group]
〇New manufacturing method.

The present inventors have established a method for preparing a compound represented by the general formula [wherein lil has the same meaning as above] and have published the following patent application.
145-40288)) continued various studies, and as a result, when the metal compound (1) was halogenated, a compound represented by the general formula [wherein R1 has the same meaning as above and X represents a halogen atom] was obtained. A metal compound is selectively obtained, and a metal compound represented by the general formula [wherein I11 has the same meaning as above] obtained by hydrolyzing the metal compound is oxidized, or a compound CI) and a compound CI) obtained by the general formula % formula % ( ) The compound represented by the general formula [in the formula, 111 and R2 have the same meanings as above] is reacted with the compound represented by the formula [in the formula, or a Vμ group], and the compound represented by the general formula [in the formula, 111 and R2 have the same meanings as above] is reacted with a halogen compound. and the general formula obtained [where nl
, R1 and Based on this discovery, the present invention was completed.

That is, the present invention provides (1) a method for producing a chemical compound (CI) characterized by oxidizing a metal compound (ff); (2) a method for producing a compound (CI) by halogenating the compound (1);
1) A method for producing compound (I), which is characterized by hydrolyzing the compound (mV) and oxidizing the obtained compound (mV), (3) reacting the compound [summer] with the compound (V), and producing the compound [
Compound CI) characterized by halogenating the compound [■] obtained by halogenating the compound [■], hydrolyzing the obtained compound [summer], and oxidizing the obtained metal compound (IV).
About the manufacturing method.

In the above formula, R is 9, for example, beniV phosphorus.

The a\μ group found in the corresponding part of cephasis l-phosphorus is conveniently adopted, and specifically nine examples include formi~, acety~, and gu! Vionoi voice, Vcroventanoi pyllio
Aliphatic carboxylic acid residue, pheni~acety~, V chloheki V, /I/aceti~s1-' chlohexen~aceti~,
1.4-dithychlorohexe V-acetyl, 2-cheni-μ acetyl, detofuzo V-acetyl, V-anoacetyl,
Substituted aliphatic groups such as phenoxyacetyl, thiacylyμ acetyl, phenylglycyl, 1-V chlohexene diμrwvv, Cheniμgly￥fi/, cyclohexedienylglyV, A/, phenylglycyl μ, etc.Oki Vbenshiμ, p-nitrivenshiμ, etc.＠−
Jlfi/bonic acid residues, etc. are used, and when these acid μ groups have an amino group, for example, tribobenzoyl V, futari μ, β-methyz-honiμ ethoxy V, It may be protected with isobonyl oxyV ρcarbon 2μ or the like. ! ? 2, for example, a V similar to R1.
A μ group may be used, and a lower aV μ group is preferably used.
'R1 may be the same or different, as X,
For example, chlorine, bromine, 0M phosphorus, and fluorine are often used.

In the method of the present invention, compound (III) is first halogenated. In this halogenation, a halogen atom is selectively introduced into the 11th position of the compound (It) instead of the 2nd position. Such surface halogenations include, for example, molecular chlorine, bromine or summer-promu-succinimide, summer-talo-mu-succinimide, chlorinated di-steel lithium heavy chloride, di-steel chloride-lithium bromide, The halogenating agents used are birylenium octopohelomide verpromide, fluoride ammonium perglomide and fluoride. Particularly suitable are halogenating agents that can be halogenated under mild conditions, such as viridinium hydropromide verpromide and phenyltrimethylanthenium verpromide.
Usually, the compound Cl0) is reacted with a halogenating agent in an equivalent amount or slightly in excess at the time described above. Halogenation proceeds advantageously in a solvent; for example, the reaction in which solvents such as chloroform, methylene chloride, ben(n), tetofhydrofuran, and dioxane are often used usually proceeds at room temperature. , heating or cooling may be performed as appropriate.

Reaction time and other reaction conditions, raw materials used.

The reaction time may be appropriately determined depending on the halogenating agent, solvent, temperature, etc., but the reaction time may also be shortened by using a radical initiator such as benzoyl peroxide or by light irradiation. The obtained compound (1) can be isolated by known means such as solvent extraction, dissolution, liquid conversion, concentration, vacuum concentration, two-fraction distillation, crystallization, recrystallization, and partition chromatography. .

Although it can be purified, the reaction solution can also be used as a raw material for the 11th step without separation.

Next, by hydrolyzing compound (1), compound (
ff) is manufactured. In this hydrolysis, the compound (
The halogen atom at position 11 in 1) is substituted with a hydroxyl group. This reaction is usually carried out in water or a mixture of water and a Ia solvent. The organic solvent may be anything that does not interfere with the reaction, such as dimethyls! Phoxyto, dimethy7@-4muamiY, yoxane, ethyl acetate μ or a mixture thereof 4111tk are frequently used. The reaction proceeds slowly at room temperature, but can be heated or cooled within a range that does not cause any problems.The reaction is usually completed within 1 to 10 hours. The obtained compound (IV) can be isolated and purified by the above-mentioned method known to Kamikai.

Next, the obtained compound (ff) is oxidized to produce compound (I). Suitable oxidizing agents include common oxidizing agents such as chromic acid, manganese dioxide, permanganate, and the like. The oxidizing agent is usually required in an amount of 1 or more equivalents per raw material (IV). These oxidizing agents are preferably eg dichloromethane, dichloroethane, chloropho! In this mixture, a halogenated hydrocarbon system such as acetone, tetophylhydrochloride, etc., or an inert solvent such as acetone, tetofhydrofluoride, etc. is allowed to act.

The reaction usually proceeds at room temperature, and when solids are involved, any conventional oxidizing method can be applied, such as stirring, which is preferred. The product [I] is, for example, an excess of reagent,
W! After removing the solvent I and unnecessary products by a conventional method, the product is purified by a conventional method such as recrystallization, chromatography, etc.

In addition, in the method of the present invention, compound (1) is reacted with compound 1:"V) or a reactive derivative thereof, and the resulting compound (Vl) is halogenated to produce the resulting compound [ (2)], the resulting compound (1) is hydrolyzed and then oxidized in the same manner as above, and the compound C
I) can also be produced.

Compound [■] is produced by reacting compound [summer] with compound [v]. Compound (V) is generally subjected to the reaction as its reactive derivative, for example, one in which the hydroxyl group of (V) is replaced with a halogen atom (for example, acetylated p-lide).

pencey μ-taloride, etc.) or an acid anhydride in which one molecule of water has been removed from two molecules of [v] (such as acetic anhydride,
The 0 reaction, in which propionic anhydride, benzoic anhydride, etc.), warm acid anhydrides, activated esters, etc. are often used, proceeds advantageously in the presence of # medium. As the solvent, for example, tethohydrofone, dioquine, M,M-dimethylacetamide, ychromamethane, etc. are used. When an acid is produced (by the reaction), the reaction proceeds more favorably when an approximately equivalent amount of a base is present. Examples of such bases include sodium hydroxide and sodium hydroxide.

Inorganic bases such as sodium hydrogen carbonate, organic bases such as trichloride, bicarbonate, etc. are often used.9 Reaction time, temperature and other reaction conditions vary depending on the raw materials, solvent, base, etc. Based on the conditions, the conditions are appropriately selected from the 0 conditions of the general ENO μS DE μ conversion reaction. The resulting compound (
VI) can be isolated and purified by the above-mentioned method, but it can also be used as a raw material for the next step as a reaction mixture.

Next, the obtained compound CVI) is halogenated to produce a compound [■]. The halogenation of the compound is achieved by employing the same reaction conditions as described for the halogenation of the compound CI). Compound [■
] is used as a raw material for the 11th reaction step of the reaction mixture after isolation using a known method.

Next, Compound [■] Compound (1) is obtained by reacting with K acid. As an acid, compound [■] (1)
For example, halogenated metal acids such as ferric chloride, tin chloride, titanium tetrachloride, halogenated nonmetallic acids such as boron trifluoride, phosphoric acid, sulfuric acid, hydrochloric acid, etc. Inorganic acids, fatty acids such as formic acid, acetic acid, trifluoro-μ acetic acid, and aromatic carboxylic acids such as benzoic acid and naphthoic acid are frequently used. The reaction is carried out in the presence or absence of an S medium. As a solvent, for example, Tetotsu kPp
Fufun, dioxane, dichloromethane.

Ben, etc. are often used.The reaction temperature, 9 hours, and other reaction conditions are appropriately determined depending on the materials, acids, solvents, etc.

In particular, compound CI) is obtained by hydrolyzing and then oxidizing the obtained compound (1) as described above.

Among the compounds thus obtained, compound Cff) is effective against fungi (richop), for which conventional 77 allos d19 is ineffective
yton rubrum, terichopytona
st*roi4es) This is a new stone with K effect.

The object compound (1) of the present invention is a new compound, and by further hydrolyzing it, a compound represented by the general formula (wherein 1 has the same meaning as above) can be obtained. This chemical compound [■] exhibits effective antibacterial activity against Guhum-positive and Oron-positive.

Hydrolysis of compound CI) is usually carried out in the presence of a base. Commonly used bases include inorganic or organic ring groups; examples of inorganic bases include sodium hydroxide, sodium borate, dibasic sodium phosphate, sodium chloride,! R-oxygen strium, etc., and as an organic base, Tatoehatoriechi! Examples include amines, *acid sodium, etc. In addition, the reaction can be advantageously advanced by using a solvent. Suitable examples of such a solvent include alcohols such as water, methanol, ethanol, etc., 2) lomethane, tetotsuto dorofubun, and acetoni, and water-containing solvents thereof. Although the scissors reaction can be carried out at room temperature, it is advantageous to carry it out under water cooling.The reaction time, other reaction conditions, and raw materials used are determined.

determined as appropriate. The resulting compound ([
) can be isolated and purified by generally known methods, such as extraction with a solvent, chromatography or recrystallization using Amberlite XAD-211 resin, silicage μ, Sephadettas, etc. You can do special things.

Reference example 1 7#-(2-chenylacetamide)-9-oxo-1
1-Pudamo 1111-Cheno C4, 3-O]-3-Sefe^7511+! Suspend in NO*30m/ and stir at room temperature for 5 hours. Methanol was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, and the ethyl acetate solution was washed with saturated brine and then dehydrated over anhydrous sodium sulfate. Distill the WI medium,
The residue was purified using V9 Kagura Tsumuta Sho Mudography [eluted with ben(noacene)one (3:1)] to give 72-
(2-Thhenylacetamido)-9-oxo-11-methoxyV-11M-cheno(4,3-a)-3-cephem 35 capes are obtained. The slippage is due to two isomers (Cu-OC”s
O” *II isomer) is hb in a y-equivalent mixture.

Engineering 11#IK訃j1t1780 (β-Tsukutam).

Otori JLX 18113, 1850 (j, A/Boni/L', 7fi
? ') Summer Mlt (Dl [8O-d6.ppm) Black &3
5. 138 (2H, each a-02-!!)#:
L75 (to 2T1 mountain-), 3.78°182 (3g, each 8.0CH3), 5.11 (111[, d, -T-
5Hz, C6-H) -5,80e 5.88 (
I H, respectively q, J-8゜5 II z, C,
, -H) -6,41,6,52(I H#each' j
"11-11[), 9.15, 9.21 (IH, respectively d, J-8Hz, N11[) Reference Example 2 II-(2-chenylacetamido)-9,11-dioxocheno[4,3- a)-3-cephem 1001Ft
50% methanol (dissolved in ~ solution and diluted with acid) 9 cum 35
Add Oki and stir at room temperature for 2 hours. After the reaction, the methanol was distilled off under reduced pressure and the aqueous layer
*ll to D-2tt hum. After washing with water, 5-stroke ethanol-μ
When eluted with , Tβ-(2-chenylacetamide)-3
-cephem-3,4-1i1μ bonic acid disodium salt 2
5Hf is obtained.

UV ＾Wed 111!1 (5F) I 237 (726G)
, 277! a&! (4840) yKB' txr1 irises 1775 (β-tuctum).

1n&X 11560 (amide), 1510 (*lvbokivv-)
) 11 [PCD, O, ppm)! 3-72.4.1?
(2H, d4.J-201x * C, -II) t
181 (2"s'p9""z-).

! 5.25 (IHa d, J -5Hz -C
6-H) -5,74(IHe d.

7m5Hs, C2 ■) 1 Reference Example 3 505G
Dissolved in medanow μ solution and added sodium hydroxide (L
Add 8f and stir for 2 hours under water cooling. After the reaction is completed, methanol is distilled off under reduced pressure, and the resulting aqueous solution is charged to Amberley)XAI)-2 cuff 5. After washing with water, 7β-pene Vμ acetamide 3-cephem-3,4-$7carboxylic acid N was eluted with 5% ethanol μ solution and as pale yellow crystals.
+) ψ ram filling 23m1F is obtained.

υma λ90%? No'''nm (g) $278 (
654G).

Otori & I 236 (41100) K! Ir -1 1Rj1@@z 61 11775 (β-tuctum)
.

18110 (amide), 16011 (** boxylate) 11 [1 (D, O, pp Otori) black 3.77 (2] 1f
, s), 3, 8.19 (211e q * J-191
m ) t 5-19 (I H-d -J-4'I
z) -5.70 (11,d, J=4Hz) Example 1 (1) 7β-(2-chenylacetamido)-9-oxo-11(2H)-chenoC4,3-c)-3- 4. Dissolve Cephem 4.1f in anhydrous tetofhydrofuran and under a nitrogen gas stream. fi 5 f's fenitrimethi~
Anthium perbromide was added in small portions over 20 minutes. After stirring for 30 minutes, the nine crystals precipitated were boiled and washed with a small amount of anhydrous tetrahydrofone. The detof and dolofuran layers were concentrated under reduced pressure at about 50 sft, and this
Add 0 m ethyl acetate μ. The ethyl acetate layer was washed with saturated brine, dried over 9 um of anhydrous sulfuric acid, and the solvent was distilled off to give Tβ-(2-chenylacetamido)-9-oxo-11-promottm- as colorless flaky crystals. 4.71 cheno(4,3-o)-3-cephem is obtained. This is yl of two isomers (α and β isomers of cu-Br):
It is a mixture of 1.

Melting point 138-143℃ (decomposition) IRw,! Iaxex +1715 (ρ-fuctum).

1700 (★~Poni*), 1661 (amide).

1630 (double bond) Ill[R (1M80-d6.ppm) $ 3.73
(2H, s.

9'c3-), 182, 193 (211,%
*aa.

J=18Hz, C2-H), 5.11.5.13(
Ht, each (!, J-5Hz, Ca-H), 5.8
0,5.83 (iJ each q, , r-4t-5Hz,
Cy-H), a, 99 (IH, s, Cx1-H), 9.
13゜&15(In, respectively d, J-gHg, NH) (phantom Tβ-(2-chenylacetamide)-9-oxo-
11-Gurosho-11H-Cheno [4,3-CI)-3
-Cephem4. Dissolve Of in 20% dimethic acid, add IWl of water to the solution, and stir at room temperature for 4 hours.
The reaction solution was poured into 400-ml ice water, and the precipitate was collected and thoroughly washed with water. This was dissolved in μml of ethyl acetate, and after active treatment, it was dehydrated with anhydrous sodium sulfate. When distilled off, pale yellow crystals Tβ-(2-chenylacetamido)-9-oxo-11-hydroxy V-11 and monocheno(4,3-e)-3-cephem 2.2f are obtained. It is an isocene compound of isomers.

Melting point: 177-179℃
, -1! H).

1LX 1782 (β-phtatum) -NMR (1M8
0-d6. ppm)! 3.30 (2II, s
, C2-H), &73(2H,8, (Il□□-),
5.01 (IH, (!', J=5.C6-H), 5.7
5 (IH, q, J-8°5 Hz, C-r-H)
, 6.28-6.43 (l H-each A 8 e C
n”H).

7.2G, 7.45CIH, 8 each, -OHD! , O
11 te disappears), 9.09 (IH, tl,
J=8Hz, 1rH) (3) 7β-(2-chenylacetamide to diS-oxo11-hydroxy$'-
-1iH-cheno [4゜3-(1)-3-cephem40
OW was dissolved in 450 ml of 1,2-dichloroethane, 5 ft of activated manganese dichloride was added thereto, and the mixture was stirred at room temperature for 50 minutes.

Mandane dioxide is milled, the furnace solution is washed with dilute hydrochloric acid and water in that order, and dehydrated with anhydrous sodium sulfate. Distill the solvent off, Iaf
li was purified by V Rikage μ column chromatography [eluted with benzene-acetone (3:, 1) and then (5:1)]
When purified by
-3-Cephem 120 da is obtained. Melting point 13B-14
0℃.

dioxane ultraviolet aa subex)μ λrB az nm (
) +236 (13870), 261 (825
G) Infrared absorption aXcs; 180
0 (β-phtatum), 1685 (unsaturation μ-bonyl).

1G60 (amide'), 1620 (double bond) magnetic resonance spectrum A' C1M80-d6, ppm)
! 3. Finished T42L! Im? -1-), 3.78.1
99 (2Ld, a.

J-8Hz p C2-H) -5-20(I H-d
-J a+6-Hz -C6-H)-5,95(lx
, qj-6;8HgeC7-H), 9.21(li.

d, J-8Hz, summer H) 1 ■L 1) Tβ-ben Ntv aceF amide 9-oxo-1
1(2K)-cheno(4,3-o)-3-cefeA 3
f t1M Water Detofhydrofuran 420 mKI was dissolved, and to this was added fe2μ trimethyammonium barb tamite & 6F under stirring at room temperature, and stirring was continued for another 1 hour. The precipitate was heated in a furnace, and the furnace liquid was concentrated in a bottle of about 405 g to give Tβ-benzylacetamide as pale yellow scaly crystals.
9-oxo-11-gwmo11111-cheno[4,
3-c)-3-cephem 2.3f is obtained. melting point 16
6-167”C (decomposition) UV λI!laxnm (c) t26B (9730)
From 2nudyol-1 wax as 11775 (β-fuctam).

171G (**devo:), 1658 (7”)'), 16
30 (double bond) N)[R(DMB O-de, ppm)!
3.53 (2H) -3,82-3,95 (2H,
Each 4dd, J-5Hz, CJ! -H) p
s, 02 C5, 14 (11, each d, 7m5E
[z, C6□-H), 5.7 (IH2 each
qs'-5)8Hz, Cfu-H)C6,95t7.
04 (IH, each As, C1x-u) (2)
7β-benzylacetamide-9-oxo-11-butamo11 to 1cheno(4,3-e)-3-cephe^3.
Of was dissolved in 15 mK1 of dimethyl sulfoxide, 111 t of water was added thereto, and the mixture was stirred at 40°C for 40 minutes. The reaction solution was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated saline, dehydrated with anhydrous sodium sulfate, and the solvent was distilled off to give oxo-11-hydroxy\-11H-cheno[4°3-e)-3-*yx 1.8 fis.
lkG:sshisu.

try λ−;, −″′am(g)+253(41
70) Engineering E "mix cii1 龜1780 (β-fuctum) summer Ml (DMB0-d6.ppm) g 3.
51(2H1s)C3,76(2I[,ri,5.00(
IH, d, J-5Hz), 5.76 (11゜q, J-5
,8Hz), 6.28(III,5)C7,2(511
1,s).

106 (115d, J-8Hz) (3) Tβ-bentytv acetamido 9-oxo-
11- and Doroki S'-11H-chenoC4,3-c,:
Dissolve 0.55 f of 1-3-cephem in 1.3 l of 1,2-dichloroethane, add activated manganese dioxide TI little by little, and stir at room temperature for 1 hour. After the reaction is completed, the manganese dioxide is removed and the solvent is removed.

＠渣をV9*GeA/Kahumukuwamatogwofi [Pen (
7β-benzylacetamine F-1.11 as pale yellow crystals.
-#Oxocheno (4',!-o) -3-*Pue 50.
21 is obtained.

Melting point 135-137'C (decomposition) IRu'::,"txi"1800Cp-Fyi>.

168T (thioanhydride), 1t6Q (amide), 16
15 (double bond) NMR (DMB0-d6.ppm)! 153(2H,s
),! , 69° 3.95 (211 [, dd), 5.17
(IH, d, J”5Tiz), 5.91 (111[e
qe'-5p 811[Z), 23
(5Js), 9.14 (IH,!, J=8Hz) Example 3 (1) 7β-(2-thiediμacetamide)-9-
Oxo-11(2H)-cheno(4,3-a)-3-cephe A1.5ft Nitromethane 85m? 2.4 m of triethyl amine and 4 m of acetic anhydride were added under ice-cooling while introducing nitrogen gas, and the mixture was returned to room temperature and stirred for 1 hour. Pour the purple reaction solution into ice water and
Add 100sf. When you take one of the precipitates and wash it with water, it becomes 1.3.
f is obtained.

IB yKBr z-": 1790 (β-'yppm>.

WL&X 1765 (eno μ acetate), 1665 (amide)
NMR (DMB0-d6, ppm) G 2.28
(3H, s, 0113) *! 77 (2L 8p
';"cHt-), 3.98 (2H mountain C2- pasting 5.
28 (I Hs 6 e C6-H-J-5Hz)
p 5.71 (1” -qe7.07 (IH mountain 01
1-H) t 7.3~7.4 (IH-1!I e
Ha) *118 (IH, 1, II, J-9Hz) (2
)Tβ-(2-thiediμacetamide)-9-ark
If8'-111-chenoC4,3-c)-3-cephem 4091 was dissolved in 5 m of ditarylomethane and stirred under water cooling.
Bromine and triethyl amine in the wall ~! Add the methane solution alternately.

After the reaction is completed, the organic layer tube is washed with an aqueous solution of hydrogen carbonate and F, dehydrated with anhydrous sodium sulfate, and removed from the solvent. The residue was purified with Vlikage μ Kahum Chroma) Gutsfi [Ben (
Elution with noacetone (9:1)] resulted in colorless phosphorus flakes. 2181 is obtained. Melting point 193-197℃ (decomposition) KBr -1 engineering & al t 3270 (-III
), 1ryo90 (βm&x-tsukuim), IT72(cH2co-), 1660(
Amido) Summer MI? CDM80-d6. 'ppm) $
2.27 (3H, B, 0COCH3).

3.75<21. s, song 1! ,! L-)-187(
3H! , C2-H containing 5.23 (I H, de
J-5H! S, C6-H), 5.73 CI H-
q 5J-5, 9Hz, C7-H) t 9. '1
8 (lus q, , T-8Hz j-HH) (3) Tβ-(2-thiediμ acetamido)-9-acetoxy$'-11-p a 4 f -c / C4# 3
- C) -3-cephem 0.3f in dichloromethane 13
Dissolve mK, cool with water, and add 2! Filled with titanium chloride 1.
Add 3- and continue stirring for an additional 15 minutes. After adding 10% hydrochloric acid, the organic layer is filtered and washed successively with a saturated aqueous sodium hydrogen oxide solution and water. After dehydration over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified using a kuri-gemu-kahumuku-tamatogufui [benzene-acetone (3:1
)] Then, colorless flaky crystals 7β-(2-acetamide)-9-oxo-11-pg-11
H-chenoC4,3-c)-3-cephem 0.17 F
is obtained. Melting point: 139-142°C.

(4) 7β-(2-thienediacetamido)-9-oxo-11-pro-11H-cheno[4,3-a)-3
-When cephem is oxidized with hydrolyzed Cu in the same manner as in Example 1-(2), (!I), 7β-(2-cheni-ace)amide)-9,if-dioxocheno[4,3-a
)-3-cephem is obtained.

Claims (1)

[Scope of Claims] (Represented by the general formula [wherein R1 has the same meaning as defined above]) characterized in that it oxidizes a compound represented by the general formula [in the formula, B represents a Vμ group] Method for producing a compound. (2) A compound represented by the general formula [in the formula, 1111 represents a Vfi/group] is halogenated, and the resulting general formula [in the formula, 11 has the same meaning as above, and X is The general formula (in the formula, 11 is the same as above-] Compound os
n decision. (2) General formula [wherein, I? 1 represents a Vμ group] and a compound represented by the general formula R''OIl [[wherein, R2 represents an y)v group] to react with a compound represented by the general formula [wherein, R2 represents an y)v group]. 11 and Bt have the same meanings as above], and the obtained general formula [in the formula,
A compound represented by the general formula [wherein 11 and and oxidizing the obtained compound represented by the general formula [wherein 11 has the same meaning as above].
Construction method.