(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

Base Information

Chemical Name:(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone
CAS No.:183504-82-7
Molecular Formula:C₂₇H₂₈ClNO₃
Molecular Weight:449.977
Hs Code.:

Synonyms:(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

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Chemical Property of (3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

Chemical Property:

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Technology Process of (3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

There total 11 articles about (3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 101104-10-3
diethyl 3-(4-chlorophenyl)glutarate

: 183504-82-7
(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

Guidance literature:: Multi-step reaction with 11 steps

1: 92 percent / α-chymotrypsin, aq. KCl / 120 h / Ambient temperature; pH 7.8

2: LiBH₄ / 1,2-dimethoxy-ethane; methanol / 1 h / Heating

3: p-toluenesulfonic acid / toluene / 3.5 h / Heating

4: 1.) n-BuLi, 3.) DIBALH / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, toluene, rt, overnight

5: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

6: 97 percent / Mg powder / 2 h / Ambient temperature

7: aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature

8: (COCl)2 / toluene / Ambient temperature

9: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

10: 1.) TiCl₄, 2.) diisopropylethylamine / 1) CH₂Cl₂, -25 deg C, 10 min; 2) CH₂Cl₂, -25 deg C, 30 min; 3) CH₂Cl₂, -25 deg C, 1 h

11: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) tetra-n-butylammonium fluoride / 1) toluene, 90 deg C, 1 h; 2) toluene, 90 deg C, 2 h

With dmap; lithium hydroxide; lithium borohydride; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; potassium chloride; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; α-chymotrypsin; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; toluene;
DOI:10.1021/jo961096b

Reference yield:

: 183504-77-0
4-(4-chlorophenyl)tetrahydro-2H-pyran-2-one

: 183504-82-7
(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi, 3.) DIBALH / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, toluene, rt, overnight

2: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

3: 97 percent / Mg powder / 2 h / Ambient temperature

4: aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature

5: (COCl)2 / toluene / Ambient temperature

6: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

7: 1.) TiCl₄, 2.) diisopropylethylamine / 1) CH₂Cl₂, -25 deg C, 10 min; 2) CH₂Cl₂, -25 deg C, 30 min; 3) CH₂Cl₂, -25 deg C, 1 h

8: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) tetra-n-butylammonium fluoride / 1) toluene, 90 deg C, 1 h; 2) toluene, 90 deg C, 2 h

With dmap; lithium hydroxide; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo961096b

Reference yield:

: (S)-3-(4-Chloro-phenyl)-5-hydroxy-pentanoic acid

: 183504-82-7
(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

Guidance literature:: Multi-step reaction with 9 steps

1: p-toluenesulfonic acid / toluene / 3.5 h / Heating

2: 1.) n-BuLi, 3.) DIBALH / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, toluene, rt, overnight

3: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

4: 97 percent / Mg powder / 2 h / Ambient temperature

5: aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature

6: (COCl)2 / toluene / Ambient temperature

7: Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / Ambient temperature

8: 1.) TiCl₄, 2.) diisopropylethylamine / 1) CH₂Cl₂, -25 deg C, 10 min; 2) CH₂Cl₂, -25 deg C, 30 min; 3) CH₂Cl₂, -25 deg C, 1 h

9: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) tetra-n-butylammonium fluoride / 1) toluene, 90 deg C, 1 h; 2) toluene, 90 deg C, 2 h

With dmap; lithium hydroxide; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo961096b