<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone

Base Information

• Chemical Name: <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone
• CAS No.: 92685-98-8
• Molecular Formula: C₂₃H₃₆ClNO₅Si
• Molecular Weight: 470.081

Synonyms:<3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone

Chemical Property of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone

There total 15 articles about <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-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: 33.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetyl chloride (92685-97-7) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone (92685-98-8) + <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-diazopropyl)-2-azetidinone

Guidance literature:

In tetrahydrofuran; at 5 - 10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

<3S-<3α(S*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate (80829-72-7) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone (92685-98-8)

Guidance literature:

Multi-step reaction with 7 steps

1: CF₃COOH / CH₂Cl₂

2: dimethylformamide; acetic acid / 0.08 h / 60 °C

3: 4-dimethylaminopyridine / dimethylformamide / 16 h / Ambient temperature

4: 37.3 percent / trimethylsilyl trifluoromethanesulphonate / CH₂Cl₂ / 16 h / 20 °C

5: 96 percent / H₂ / 10percent palladium / ethyl acetate

6: oxalyl chloride / tetrahydrofuran / 12 h / Ambient temperature

7: 6.4 percent / tetrahydrofuran / 1.) 5 deg C, 2.) 30 min., room temp.

With dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; trifluoroacetic acid; palladium; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)91132-9

Reference yield:

t-butyl N-(2,4-dimethoxybenzyl)glycinate (81902-60-5) → <3S-<3α(S*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-(2-oxo-3-chloropropyl)-2-azetidinone (92685-98-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 84 percent / N,N-dicyclohexylcarbodiimide / tetrahydrofuran / 0.25 h / 20 - 25 °C

2: 1.) LiN(SiMe₃)2, 2.) LiN(SiMe₃)2 / 1.) THF, 15 min., from 0 deg C to 5 deg C, 2.) from 20 deg C to 25 deg C, THF, 1 h.

3: CF₃COOH / CH₂Cl₂

4: dimethylformamide; acetic acid / 0.08 h / 60 °C

5: 4-dimethylaminopyridine / dimethylformamide / 16 h / Ambient temperature

6: 37.3 percent / trimethylsilyl trifluoromethanesulphonate / CH₂Cl₂ / 16 h / 20 °C

7: 96 percent / H₂ / 10percent palladium / ethyl acetate

8: oxalyl chloride / tetrahydrofuran / 12 h / Ambient temperature

9: 6.4 percent / tetrahydrofuran / 1.) 5 deg C, 2.) 30 min., room temp.

With dmap; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium hexamethyldisilazane; palladium; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)91132-9

upstream raw materials:

diazomethane

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(2,4-dimethoxy-benzyl)-4-oxo-azetidin-2-yl]-acetyl chloride

2,4-dimethoxybenzylamine hydrochloride

<3S-<3α(S^*),4β>>-benzyl<1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

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