1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide

Base Information

• Chemical Name: 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide
• CAS No.: 370064-93-0
• Molecular Formula: C₂₈H₃₂N₂O₅S
• Molecular Weight: 508.638

Synonyms:1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide

Chemical Property of 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide

Chemical Property:

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Technology Process of 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide

There total 9 articles about 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide 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: 69.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid (370064-92-9) → 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide (370064-93-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)00641-X

Reference yield:

(E)-8-phenyloct-2-enoic acid methyl ester (144809-41-6) → 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide (370064-93-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / LiOH / H₂O; tetrahydrofuran / 48 h / 45 °C

2.1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 3.5 h / 0 - 20 °C

3.1: 1.40 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.1: 93 percent / Bu₂BOTf / CH₂Cl₂ / 1 h / -78 °C

5.1: Me₂AlCl / CH₂Cl₂ / 0.33 h / 0 °C

5.2: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

6.1: 93 percent / n-BBuLi / tetrahydrofuran / 2 h / 0 °C

7.1: 91 percent / Et₃N; BnOH / CH₂Cl₂ / 48 h / 20 °C

8.1: 86 percent / H₂ / 10 percent Pd/C / ethanol / 16 h / 760 Torr

9.1: 69 percent / EDC; HOBt; N-methyl morpholine / tetrahydrofuran

With 4-methyl-morpholine; lithium hydroxide; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethylaluminum chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; benzyl alcohol; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00641-X

Reference yield:

(E)-8-phenyloct-2-enoic acid chloride → 1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid benzyloxyamide (370064-93-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1.40 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.1: 93 percent / Bu₂BOTf / CH₂Cl₂ / 1 h / -78 °C

3.1: Me₂AlCl / CH₂Cl₂ / 0.33 h / 0 °C

3.2: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 93 percent / n-BBuLi / tetrahydrofuran / 2 h / 0 °C

5.1: 91 percent / Et₃N; BnOH / CH₂Cl₂ / 48 h / 20 °C

6.1: 86 percent / H₂ / 10 percent Pd/C / ethanol / 16 h / 760 Torr

7.1: 69 percent / EDC; HOBt; N-methyl morpholine / tetrahydrofuran

With 4-methyl-morpholine; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dimethylaluminum chloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; benzyl alcohol; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)00641-X

upstream raw materials:

O-benzylhydoxylamine hydrochloride

1-(4-methoxybenzenesulfonyl)-3-(S)-(5-phenylpentyl)aziridine-2-(R)-carboxylic acid

(E)-8-phenyloct-2-enoic acid methyl ester

(E)-8-phenyloct-2-enoic acid

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