(S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Base Information

• Chemical Name: (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone
• CAS No.: 335160-71-9
• Molecular Formula: C₂₆H₃₄N₂O₈S
• Molecular Weight: 534.631

Synonyms:(S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Chemical Property of (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

Chemical Property:

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Technology Process of (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone

There total 10 articles about (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone 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: 83.0%

benzenesulfonyl chloride (98-09-9) + (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-(2-hydroxyethyl)-2-piperazinone (335160-69-5) → (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone (335160-71-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol015504w

Reference yield:

2,4-dimethoxybenzylamine hydrochloride (20781-21-9) → (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone (335160-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: 93 percent / NaHCO₃ / ethyl acetate; H₂O / 0.33 h / 0 °C

3.1: 75 percent / Cs₂CO₃ / dimethylformamide / 2 h / 65 °C

4.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 7 h

4.2: 96 percent / NaIO₄; NaHCO₃ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h

5.1: 92 percent / NaBH₄ / ethanol / 1 h / 0 - 20 °C

6.1: 83 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol015504w

Reference yield:

tert-butyl (S)-(1-oxopent-4-en-2-yl)carbamate (95107-99-6) → (S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-[2-(phenylsulfonyloxy)ethyl]-2-piperazinone (335160-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 14 h / 20 °C

2.1: 93 percent / NaHCO₃ / ethyl acetate; H₂O / 0.33 h / 0 °C

3.1: 75 percent / Cs₂CO₃ / dimethylformamide / 2 h / 65 °C

4.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 7 h

4.2: 96 percent / NaIO₄; NaHCO₃ / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 1.5 h

5.1: 92 percent / NaBH₄ / ethanol / 1 h / 0 - 20 °C

6.1: 83 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ol015504w

upstream raw materials:

benzenesulfonyl chloride

(S)-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-5-(2-hydroxyethyl)-2-piperazinone

2,4-dimethoxybenzylamine hydrochloride

tert-butyl (S)-(1-oxopent-4-en-2-yl)carbamate

Downstream raw materials:

1(R),5(S)-8-tert-butoxycarbonyl-3-(2,4-dimethoxybenzyl)-3,8-diaza-2-oxobicyclo[3.2.1]octane

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