N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

Base Information

Chemical Name:N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester
CAS No.:444344-92-7
Molecular Formula:C₂₄H₃₂N₂O₇
Molecular Weight:460.527
Hs Code.:

Synonyms:N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

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Chemical Property of N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

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Technology Process of N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

There total 5 articles about N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl 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: 72.0%

: 23150-65-4
L-glutamic dimethyl ester hydrochloride

: 444344-91-6
4-[[(benzyloxy)carbonyl]amino]-bicyclo[2.2.2]octane-1-carboxylic acid

: 444344-92-7
N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

Guidance literature:: With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at -5 - 20 ℃;
DOI:10.1016/S0223-5234(01)01224-7

Reference yield:

: 834-50-4
4-(ethoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

: 444344-92-7
N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: diphenylphosphoryl azide; Et₃N / toluene / 1 h / 20 °C

2: toluene / 0.75 h / Heating

3: 9.53 g / toluene / 18 h / Heating

4: 85 percent / aq. NaOH / ethanol / 21 h / 20 - 65 °C

5: 72 percent / diphenylphosphoryl azide; Et₃N / dimethylformamide / -5 - 20 °C

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In ethanol; N,N-dimethyl-formamide; toluene; 2: Curtius rearrangement;
DOI:10.1016/S0223-5234(01)01224-7

Reference yield:

: 4-isocyanato-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester

: 444344-92-7
N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 9.53 g / toluene / 18 h / Heating

2: 85 percent / aq. NaOH / ethanol / 21 h / 20 - 65 °C

3: 72 percent / diphenylphosphoryl azide; Et₃N / dimethylformamide / -5 - 20 °C

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0223-5234(01)01224-7