N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester
• CAS No.: 436849-00-2
• Molecular Formula: C₂₀H₂₂ClNO₅
• Molecular Weight: 391.851
• Mol file: 436849-00-2.mol

Synonyms:N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester

Chemical Property of N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester

There total 4 articles about N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl 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:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester (436849-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / aq. Na₂CO₃ / tetrahydrofuran

2: 87 percent / NaHCO₃ / dimethylformamide / 12 h / 0 - 20 °C

With sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0212314

Reference yield:

L-Chp-OH → N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester (436849-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / aq. Na₂CO₃ / tetrahydrofuran

2: 87 percent / NaHCO₃ / dimethylformamide / 12 h / 0 - 20 °C

With sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0212314

Reference yield:

(S)-hydroxyphenylglycine (32462-30-9) → N-tert-butoxycarbonyl-(S)-3-chloro-4-hydroxyphenylglycine benzyl ester (436849-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; sulfuryl dichloride / 16 h / 20 °C / Inert atmosphere

2: sodium hydrogencarbonate / tetrahydrofuran; water / 16 h / 0 - 20 °C / Inert atmosphere

3: sodium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

With sulfuryl dichloride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201403577

upstream raw materials:

di-tert-butyl dicarbonate

(S)-hydroxyphenylglycine

Downstream raw materials:

N-tertbutoxycarbonyl-(S)-3-chloro-4-(tert-butyldimethylsilyloxy)phenylglycine benzyl ester

Boc-L-Ala-D-Ala-L-(3-chloro-4-hydroxyphenylglycine)-OBn

Boc-L-Ala-D-Ala-L-(3-chloro-4-hydroxyphenylglycine)-OH

Fmoc-L-(2,3-diaminopropionic acid)(Boc-L-Ala-D-Ala-L-(3-chloro-4-hydroxyphenylglycine))-OBn

Refernces

• 1、 -. "NOVEL CHONDRAMIDE DERIVATIVES". . . Retrieved 2015/11/17.
• 2、 Jiang, Wanlong,Wanner, Jutta,Lee, Richard J.,Bounaud, Pierre-Yves,Boger, Dale L.. "Total synthesis of the ramoplanin A2 and ramoplanose aglycon". . p. 5288 - 5290. Retrieved 2007/10/03.