methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Base Information

• Chemical Name: methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate
• CAS No.: 215719-43-0
• Molecular Formula: C₃₄H₄₄N₄O₁₀
• Molecular Weight: 668.744
• Mol file: 215719-43-0.mol

Synonyms:methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Chemical Property of methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

There total 14 articles about methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate 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: 80.0%

Z-D(tBu)-OH (5545-52-8) + methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-42-9) → methyl {N2-[(benzyloxy)carbonyl]-O4-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-43-0)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane;

DOI:10.1039/a804412k

Reference yield:

(2S,3R,4R)-4-Benzoylamino-3-tert-butoxycarbonylamino-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester → methyl {N2-[(benzyloxy)carbonyl]-O4-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-43-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.26 g / ethyl acetate; diethyl ether

2: 96 percent / H₂ / Pd/C / dimethylformamide / 36 h

3: 80 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Esterification / 2: Catalytic hydrogenation / 3: Acylation;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

Reference yield:

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-37-2) → methyl {N2-[(benzyloxy)carbonyl]-O4-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / H₂ / Pd/C / dimethylformamide / 36 h

2: 80 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

With 1-hydroxy-7-aza-benzotriazole; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Acylation;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

upstream raw materials:

Z-D(tBu)-OH

methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Downstream raw materials:

((3S,7R,8R,8aS)-8-Amino-7-benzoylamino-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-acetic acid

tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate