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Cas Database

27068-88-8

27068-88-8

Identification

Synonyms:1,5-Benzothiazepin-4(5H)-one,2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)- (8CI)

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 13 Articles be found

Solid phase synthesis of hydroxy benzothiazepinones through cyclative release under thermolysis

Sampath Kumar,Pawan Chakravarthy,Shesha Rao,Joyasawal, Sipak,Yadav

, p. 888 - 889 (2007/10/03)

Hydroxy benzothiazepinones were synthesized by a simple procedure involving epoxidation of polymer bound cinnamic acids followed by nucleophilic opening of the resulting glycidic ester by o-aminothiophenol to afford the intermediate hydroxy anilino-esters which underwent cyclization cleavage on heating in DMF to release the product completely.

Process for preparing an optically active phenylglycidyl acid derivative

-

, (2008/06/13)

The invention relates to a process for preparing an optically active trans-compound having formula (1), in which R represents a phenyl group, whether or not substituted, preferably p-methoxyphenyl, and A is derived from an optically active compound, in which an aldehyde having formula (2), in which R is as defined above, is, in the presence of a base, brought into contact with an optically active acetyl compound having formula (3), in which X represents a leaving group and in which A is derived from an amino alcohol, preferably a beta -amino alcohol having a rigid structure. Particularly good results were obtained when use was made of a compound having formula (3), in which A is derived from an amino indanol compound having formula (4), in which R1 and R2 represent a (hetero)alkyl or (hetero)aryl group, whether or not substituted, having 1-10 C atoms, or R1 and R2 constitute an aromatic or aliphatic ring together with the N atom to which they are bound, in particular in which R1 and R2 each independently of one another represent methyl, ethyl, isopropyl, n-propyl, n-butyl, allyl, benzyl or tosyl.

Optical resolution of a 1,5-benzothiazepine derivative, a synthetic intermediate of diltiazem, by preferential crystallization and diastereomeric salt formation

Yamada, Shin-Ichi,Yoshioka, Ryuzo,Shibatani, Takeji

, p. 1922 - 1927 (2007/10/03)

Practical preparation methods of an optically active intermediate of diltiazem, (+)-(2S,3S)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2- (4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(+)-7], have been developed by the use of physicochemical and chemical resolutions. 1) The salt of (+)-7 with 3-amino-4-hydroxy-benzenesulfonic acid (AHS), was found to exist as a conglomerate and could be reproducibly resolved into (+)-7·AHS and (-)- 7·AHS of 94-98% ee by a preferential crystallization procedure. 2) (+)- (1R)-3-Bromocamphor-9-sulfonic acid [(+)-BCS] was found to be an efficient resolving agent for (±)-7 and the diastereomeric resolution provided (+)- 7·(+)-BCS·2H2O salt in >43% yield and >97% ee by fractional crystallization. It is presumed that the crystal water of (+)-7·(+)- BCS·2H2O plays an important role in the selective crystallization during this efficient resolution.

Process for the preparation of a benzothiazepine

-

, (2008/06/13)

Process for the preparation of a 1,5-benzothiazepine derivative, or a salt thereof, of formula 1 where R1 represents H, an alkyl group or an alkoxy group and R2represents H or a halogen, in which process a propanoic acid derivative of formula 2 where R1and R2are as defined above and R3represents H or an alkyl group is subjected to an intramolecular cyclisation reaction in a non-halogenated solvent in the presence of a carboxylic acid. Preferably, R2is H and R1is OCH3.Trichloroacetic acid is preferablky used as α-chlorinated acid. The benzothiazepine obtained on cyclisation can be subjected to an alkylation reaction and/or an acylation reaction to obtain known pharmaceutical products, in particular diltiazem.

A microwave synthesis of the cis and trans isomers of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one : The influence of solvent and power output on the diastereoselectivity

Vega, Juan A.,Cueto, Senida,Ramos, Andres,Vaquero, Juan J.,Garcia-Navio, Jose L.,Alvarez-Builla, Julio,Ezquerra, Jesus

, p. 6413 - 6416 (2007/10/03)

A diastereoselective one-pot synthesis and the trans- and cis-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H) -one nucleus, a key intermediate in the preparation of the calcium channel blocker Diltiazem, is carried out under microwave irradiation in an open vessel. Control of the diastereoselectivity is achieved by varying the reaction time and power output as well as the nature of the solvent.

Process route upstream and downstream products

Process route

(2S,3S)-3-(2-aminophenyl)thio-2-hydroxy-3-4-methoxybenzene propanoic acid

(2S,3S)-3-(2-aminophenyl)thio-2-hydroxy-3-4-methoxybenzene propanoic acid

p-toluenesulfonic acid monohydrate
6192-52-5

p-toluenesulfonic acid monohydrate

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid
42399-48-4

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
27068-88-8

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
42399-49-5

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Conditions
Conditions Yield
10.8 g (88%)
(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester
30193-56-7

(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester

methanol
67-56-1

methanol

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
27068-88-8

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Conditions
Conditions Yield
With trichloroacetic acid; In o-xylene;
methyl trans-3-(4-methoxyphenyl)glycidate
96125-49-4

methyl trans-3-(4-methoxyphenyl)glycidate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester
30193-56-7

(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

(+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

(+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
Conditions Yield
In toluene; for 0.166667h; Yields of byproduct given; Irradiation; microwave, 350 watts;
21%
methyl trans-3-(4-methoxyphenyl)glycidate
96125-49-4

methyl trans-3-(4-methoxyphenyl)glycidate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester
30193-56-7

(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

(+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

(+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
Conditions Yield
In toluene; for 0.166667h; Yields of byproduct given; Irradiation; microwave, 350 watts;
21%
cis-(+/-)-2,3-dihydro-3-<(2-methoxyethoxy)methoxy>-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

cis-(+/-)-2,3-dihydro-3-<(2-methoxyethoxy)methoxy>-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Conditions
Conditions Yield
With titanium tetrachloride; In dichloromethane; at 0 ℃;
92%
(+/-)-(R*,R*)-β-<(2-aminophenyl)thio>-α-hydroxy-4-methoxybenzenepropanoic acid
30193-57-8,30825-31-1,42399-48-4,42399-50-8,42399-55-3,119009-50-6,131565-75-8,131613-02-0

(+/-)-(R*,R*)-β-<(2-aminophenyl)thio>-α-hydroxy-4-methoxybenzenepropanoic acid

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Conditions
Conditions Yield
In xylene; at 135 ℃; for 9h;
84%
for 11h; Heating;
42%
3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionic acid

3-(2-Amino-phenylsulfanyl)-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionic acid

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

cis-(+/-)-2,3-dihydro-3-<(2-methoxyethoxy)methoxy>-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

cis-(+/-)-2,3-dihydro-3-<(2-methoxyethoxy)methoxy>-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Conditions
Conditions Yield
With 4 A molecular sieve; In xylene; Heating;
50%
7%
ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate
154076-93-4

ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
2: 5percent aq. NaOH / Ambient temperature
3: 7 percent / 4 Angstroem molecular sieves / xylene / Heating
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; In tetrahydrofuran; xylene;
Multi-step reaction with 4 steps
1: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
2: 5percent aq. NaOH / Ambient temperature
3: 50 percent / 4 Angstroem molecular sieves / xylene / Heating
4: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; titanium tetrachloride; In tetrahydrofuran; dichloromethane; xylene;
Multi-step reaction with 3 steps
1: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
2: 90 percent / trimethylaluminum / hexane; CH2Cl2 / 1 h / Ambient temperature
3: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With n-butyllithium; trimethylaluminum; titanium tetrachloride; In tetrahydrofuran; hexane; dichloromethane;
3-Hydroxy-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionic acid ethyl ester

3-Hydroxy-2-(2-methoxy-ethoxymethoxy)-3-(4-methoxy-phenyl)-propionic acid ethyl ester

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 49 percent / Et3N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 5percent aq. NaOH / Ambient temperature
4: 7 percent / 4 Angstroem molecular sieves / xylene / Heating
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; xylene;
Multi-step reaction with 5 steps
1: 49 percent / Et3N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 5percent aq. NaOH / Ambient temperature
4: 50 percent / 4 Angstroem molecular sieves / xylene / Heating
5: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; titanium tetrachloride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; xylene;
Multi-step reaction with 4 steps
1: 49 percent / Et3N, 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 90 percent / trimethylaluminum / hexane; CH2Cl2 / 1 h / Ambient temperature
4: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With n-butyllithium; trimethylaluminum; titanium tetrachloride; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
ethyl 3-fluoro-2-<(2-methoxyethoxy)methoxy>-3-(4-methoxylphenyl)-2-propionate

ethyl 3-fluoro-2-<(2-methoxyethoxy)methoxy>-3-(4-methoxylphenyl)-2-propionate

3<i>c</i>-hydroxy-2<i>r</i>-(4-methoxy-phenyl)-2,3-dihydro-5<i>H</i>-benzo[<i>b</i>][1,4]thiazepin-4-one
27068-88-8,30825-34-4,42399-49-5,42399-51-9,89646-44-6,101143-20-8,107438-58-4,132830-16-1,132830-17-2

3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 59 percent / DBU / 9 h / 150 °C
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 5percent aq. NaOH / Ambient temperature
4: 7 percent / 4 Angstroem molecular sieves / xylene / Heating
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; xylene;
Multi-step reaction with 5 steps
1: 59 percent / DBU / 9 h / 150 °C
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 5percent aq. NaOH / Ambient temperature
4: 50 percent / 4 Angstroem molecular sieves / xylene / Heating
5: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With sodium hydroxide; n-butyllithium; 4 A molecular sieve; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; xylene;
Multi-step reaction with 4 steps
1: 59 percent / DBU / 9 h / 150 °C
2: 85 percent Spectr. / BuLi / tetrahydrofuran / 5 h / 70 °C
3: 90 percent / trimethylaluminum / hexane; CH2Cl2 / 1 h / Ambient temperature
4: 92 percent / TiCl4 / CH2Cl2 / 0 °C
With n-butyllithium; trimethylaluminum; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; hexane; dichloromethane;

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