N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine
• CAS No.: 193073-75-5
• Molecular Formula: C₁₄H₁₇Cl₂NO₅
• Molecular Weight: 350.199
• Mol file: 193073-75-5.mol

Synonyms:N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine

Chemical Property of N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine

There total 6 articles about N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine 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: 67.0%

methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-methoxyphenyl)acetate (191542-08-2) → N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine (193073-75-5)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1016/S0040-4039(97)00938-6

Reference yield:

[(R)-(3,5-dichloro-4-methoxyphenyl)-(S)-(2-hydroxy-1-phenylethylamino)]acetic acid methyl ester (193073-53-9) → N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine (193073-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Pb(OAc)4; phosphate buffer / CH₂Cl₂; methanol / 0.5 h / 0 °C / pH 7

1.2: 82 percent / HCl / diethyl ether / 3 h / 20 °C

2.1: 92 percent / N(C₂H₅)3 / tetrahydrofuran / 5 h / 20 °C

3.1: 67 percent / aq. K₂CO₃ / methanol / 2 h / 20 °C

With lead(IV) acetate; phosphate buffer; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: oxidative cleavage / 1.2: Hydrolysis / 2.1: Acylation / 3.1: Hydrolysis;

DOI:10.3987/COM-99-8514

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-(R)-(3,5-dichloro-4-methoxy)phenylglycine (193073-75-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NEt₃ / tetrahydrofuran

2: 67 percent / K₂CO₃ / methanol

With potassium carbonate; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(97)00938-6

upstream raw materials:

methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-methoxyphenyl)acetate

di-tert-butyl dicarbonate

[(R)-(3,5-dichloro-4-methoxyphenyl)-(S)-(2-hydroxy-1-phenylethylamino)]acetic acid methyl ester

(R)-Amino-(3,5-dichloro-4-methoxy-phenyl)-acetic acid methyl ester

Downstream raw materials:

[2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester

(S)-[(S)-2-{[(R)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester

[2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(S)-(4-methoxyphenyl)acetic acid methyl ester

[2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester