(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester

Base Information

• Chemical Name: (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester
• CAS No.: 873841-01-1
• Molecular Formula: C₂₈H₃₄Cl₂N₂O₇
• Molecular Weight: 581.493
• Mol file: 873841-01-1.mol

Synonyms:(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester

Chemical Property of (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester

There total 8 articles about (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl 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: 77.0%

(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-vinylprolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosine methyl ester (873840-99-4) → (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester (873841-01-1)

Guidance literature:

(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-vinylprolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosine methyl ester; With ozone; In dichloromethane; at -78 ℃;

With sodium tris(acetoxy)borohydride; In dichloromethane; at -78 - 20 ℃; for 24h;

DOI:10.1021/jo0517287

Reference yield:

(3R,7aR)-3-(trichloromethyl)-7a-vinyltetrahydropyrrolo[1,2-c]oxazol-1(3H)-one (873840-90-5) → (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester (873841-01-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetyl chloride / 168 h / 20 °C

2.1: 73 percent / ethyldiisopropylamine / CH₂Cl₂ / 60 h / 20 °C

3.1: NaOH / H₂O; methanol / 1 h / 50 °C

4.1: 92 percent / HATU; ethyldiisopropylamine / 1-methyl-pyrrolidin-2-one / 0.42 h

5.1: ozone / CH₂Cl₂ / -78 °C

5.2: 77 percent / Na[BH(OAc)3] / CH₂Cl₂ / 24 h / -78 - 20 °C

With sodium hydroxide; ozone; N-ethyl-N,N-diisopropylamine; acetyl chloride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water;

DOI:10.1021/jo0517287

Reference yield:

(R)-1-tert-butyl 2-methyl 2-vinylpyrrolidine-1,2-dicarboxylate (873840-92-7) → (2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester (873841-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaOH / H₂O; methanol / 1 h / 50 °C

2.1: 92 percent / HATU; ethyldiisopropylamine / 1-methyl-pyrrolidin-2-one / 0.42 h

3.1: ozone / CH₂Cl₂ / -78 °C

3.2: 77 percent / Na[BH(OAc)3] / CH₂Cl₂ / 24 h / -78 - 20 °C

With sodium hydroxide; ozone; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water;

DOI:10.1021/jo0517287

upstream raw materials:

(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-vinylprolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosine methyl ester

(2R,3R)-4-oxo-2-(trichloromethyl)-1-aza-3-oxabicyclo[3.3.0]octane-5-carbaldehyde

(3R,7aR)-3-(trichloromethyl)-7a-vinyltetrahydropyrrolo[1,2-c]oxazol-1(3H)-one

(R)-1-tert-butyl 2-methyl 2-vinylpyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester