(S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester

Base Information

• Chemical Name: (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester
• CAS No.: 1214908-96-9
• Molecular Formula: C₂₀H₃₁NO₆
• Molecular Weight: 381.469
• Mol file: 1214908-96-9.mol

Synonyms:(S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester

Chemical Property of (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester

There total 2 articles about (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester 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: 73.0%

(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (18938-60-8) + 2-bromoethanol (540-51-2) → (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester (1214908-96-9)

Guidance literature:

(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate; With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 0.666667h; Inert atmosphere;

2-bromoethanol; In N,N-dimethyl-formamide; for 48h; Inert atmosphere;

DOI:10.1002/chem.201202474

Reference yield:

Boc-Tyr-OH (3978-80-1) → (S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester (1214908-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / N,N-dimethyl acetamide / 48 h / 55 °C / Inert atmosphere

2.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / N,N-dimethyl-formamide / 0.67 h / 50 °C / Inert atmosphere

2.2: 48 h / Inert atmosphere

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1002/chem.201202474

Reference yield: 83.0%

(S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-hydroxyethoxy)phenyl]propionic acid tert-butyl ester (1214908-96-9) + 6-(4-chlorosulfonyl-phenyl)hexanoic acid methyl ester (1425707-83-0) → (S)-(+)-6-(4-(2-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylaminoethyl)phenoxy]ethoxysulfonyl)phenyl)hexanoic acid methyl ester (1425708-10-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1.75h; Inert atmosphere;

DOI:10.1002/chem.201202474

upstream raw materials:

(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

2-bromoethanol

Boc-Tyr-OH

Downstream raw materials:

(S)-(+)-6-(4-[2-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylaminoethyl)phenoxy]ethoxysulfonyl]phenyl)hexanoic acid

(S)-(+)-2-tert-butoxycarbonylamino-3-[4-(2-fluoroethoxy)phenyl]propionic acid tert-butyl ester

(S)-(+)-6-(4-(2-[4-(2-tert-butoxycarbonyl-2-tert-butoxycarbonylaminoethyl)phenoxy]ethoxysulfonyl)phenyl)hexanoic acid methyl ester