p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate

Base Information

• Chemical Name: p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate
• CAS No.: 81868-03-3
• Molecular Formula: C₂₃H₁₉NO₆
• Molecular Weight: 405.407
• Mol file: 81868-03-3.mol

Synonyms:

Chemical Property of p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate

There total 1 articles about p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate 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:

malonic acid (141-82-2) + 1-bromomethyl-4-nitro-benzene (100-11-8) + diazodiphenylmethane (908093-98-1) → p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate (81868-03-3)

Guidance literature:

With TEA; Multistep reaction; 1.) ether, RT; 2.) dioxane;

DOI:10.1248/cpb.33.3299

Reference yield:

p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate (81868-03-3) → (R)-4-3'-diazo-3'-p-nitrobenzyloxycarbonyl-2'-oxopropyl-2-azetidinone (82290-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) isobutyl chloroformate, TEA; 2.) 50 percent NaH / 1.) THF, -20 deg C, 1 h; 2.) -5- 5 deg C, 1 h, THF

2: 91 percent / trifluoroacetic acid, anisole / 0.33 h / -5 - -2 °C

3: 90 percent / TEA, p-carboxybenzenesulfonyl azide / acetonitrile / 1 h / Ambient temperature

With TEA; p-carboxybenzenesulfonyl azide; sodium hydride; methoxybenzene; trifluoroacetic acid; isobutyl chloroformate; In acetonitrile;

DOI:10.1248/cpb.33.3299

Reference yield:

p-nitrobenzyl (diphenylmethyloxycarbonyl)acetate (81868-03-3) → p-nitrobenzyl (5S,2'R)-2-2'-p-nitrobenzyloxycarbonyl-2'-p-nitrobenzyloxycarbonylaminoethylthio-1-carba-2-penem-3-carboxylate (103841-73-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) isobutyl chloroformate, TEA; 2.) 50 percent NaH / 1.) THF, -20 deg C, 1 h; 2.) -5- 5 deg C, 1 h, THF

2: 91 percent / trifluoroacetic acid, anisole / 0.33 h / -5 - -2 °C

3: 90 percent / TEA, p-carboxybenzenesulfonyl azide / acetonitrile / 1 h / Ambient temperature

4: 92 percent / Rh₂(OAc)4 / benzene / 0.75 h / 80 - 85 °C

5: 1.) N,N-diisopropylethylamine, diphenyl phosphorochloridate; 2.) N,N-diisopropylethylamine / 1.) CH₃CN, -10- -8 deg C, 1 h; 2.) CH₃CN, -10 deg C, 10 min

With dirhodium tetraacetate; TEA; p-carboxybenzenesulfonyl azide; sodium hydride; methoxybenzene; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; trifluoroacetic acid; isobutyl chloroformate; In acetonitrile; benzene;

DOI:10.1248/cpb.33.3299

upstream raw materials:

malonic acid

1-bromomethyl-4-nitro-benzene

diazodiphenylmethane

Downstream raw materials:

(R)-4-3'-diphenylmethyloxycarbonyl-3'-p-nitrobenzyloxycarbonyl-2'-oxopropyl-2-azetidinone

p-nitrobenzyl (5S,2'R)-2-2'-p-nitrobenzyloxycarbonyl-2'-p-nitrobenzyloxycarbonylaminoethylthio-1-carba-2-penem-3-carboxylate

(R)-4-3'-p-nitrobenzyloxycarbonyl-2'-oxopropyl-2-azetidinone

p-nitrobenzyl (3R,5R)-1-carba-2-oxopenam-3-carboxylate