(S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate

Base Information

• Chemical Name: (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate
• CAS No.: 1450880-90-6
• Molecular Formula: C₂₃H₂₈N₂O₅S
• Molecular Weight: 444.552
• Mol file: 1450880-90-6.mol

Synonyms:(S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate

Chemical Property of (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate

There total 2 articles about (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate 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: 64.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (E)-3-(phenylsulfonyl)prop-2-en-1-amine hydrochloride (1450880-89-3) → (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate (1450880-90-6)

Guidance literature:

N-tert-butoxycarbonyl-L-phenylalanine; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.5h;

(E)-3-(phenylsulfonyl)prop-2-en-1-amine hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2018.05.005

Reference yield:

(E)-tert-butyl 3-(phenylsulfonyl)allylcarbamate (1450880-88-2) → (S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate (1450880-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetyl chloride / ethyl acetate; ethanol / 18 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.5 h / 20 °C

2.2: 20 °C

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; acetyl chloride; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1016/j.bmcl.2018.05.005

Reference yield: 81.0%

(S,E)-tert-butyl 1-oxo-3-phenyl-1-(3-(phenylsulfonyl)allylamino)-propan-2-ylcarbamate (1450880-90-6) → (S,E)-2-amino-3-phenyl-N-(3-(phenylsulfonyl)allyl)propanamide (1450880-91-7)

Guidance literature:

With methanol; acetyl chloride; In ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.1039/c3ob41341a

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(E)-3-(phenylsulfonyl)prop-2-en-1-amine hydrochloride

(E)-tert-butyl 3-(phenylsulfonyl)allylcarbamate

Downstream raw materials:

(S,E)-2-amino-3-phenyl-N-(3-(phenylsulfonyl)allyl)propanamide