1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid, 4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[ [(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-, bis[(4-nitrophenyl)methyl] ester

Base Information

Chemical Name:1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid, 4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[ [(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-, bis[(4-nitrophenyl)methyl] ester
CAS No.:65750-54-1
Molecular Formula:C42H37BrN6O18S
Molecular Weight:1025.76
Hs Code.:

1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid,
4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[
[(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-,
bis[(4-nitrophenyl)methyl] ester

Synonyms:

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Chemical Property of 1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid, 4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[ [(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-, bis[(4-nitrophenyl)methyl] ester

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Technology Process of 1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid, 4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[ [(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-, bis[(4-nitrophenyl)methyl] ester

There total 23 articles about 1-Azabicyclo[3.2.0]heptane-2,2-dicarboxylic acid, 4-bromo-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-6-[1-[[ [(4-nitrophenyl)methoxy]carbonyl]oxy]ethyl]-7-oxo-, bis[(4-nitrophenyl)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:

: 65750-59-6
2-(4-nitrobenzyloxycarbonylamino)ethanethiol

: 65750-54-1
(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

Guidance literature:: Multi-step reaction with 6 steps

1: BF₃*Et₂O / acetonitrile / 3 h / 0 °C

2: 1.) Br₂; 2.) Et₃N / 1.) pentane, THF, ether, 0 deg C, 10 min; 2.) cyclohexene; 3.) Et₃N, DMF, r.t. 2 h

3: 26 percent / tetrahydrofuran; toluene / 2.5 h / Heating

4: SOCl₂/pyridine / tetrahydrofuran / 1.) 5 min, -20 deg C; 2.) 0.5 h, 0 deg C; 3.) 1 h, 25 deg C

5: 57 percent / Bu₃P, K₂HPO₄ / dimethylformamide; H₂O / 0.58 h

6: 1.) Br₂ ; 2.) Et₃N / 1.) pentane, THF/ether, 15 min, 0 deg C; 2.) DMF, 2 h, r.t.

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo01294a044

Reference yield:

: 65750-59-6
2-(4-nitrobenzyloxycarbonylamino)ethanethiol

: 65750-54-1
(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

Guidance literature:: Multi-step reaction with 6 steps

1: BF₃*Et₂O / acetonitrile / 3 h / 0 °C

2: 1.) Br₂; 2.) Et₃N / 1.) pentane, THF, ether, 0 deg C, 10 min; 2.) cyclohexene; 3.) Et₃N, DMF, r.t. 2 h

3: 41 percent / tetrahydrofuran; toluene / 2.5 h / Heating

4: SOCl₂/pyridine / tetrahydrofuran / 1.) 5 min, -20 deg C; 2.) 0.5 h, 0 deg C; 3.) 1 h, 25 deg C

5: 69 percent / Bu₃P, K₂HPO₄ / dimethylformamide; H₂O / 0.58 h

6: 1.) Br₂ ; 2.) Et₃N / 1.) pentane, THF/ether, 15 min, 0 deg C; 2.) DMF, 2 h, r.t.

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; boron trifluoride diethyl etherate; bromine; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo01294a044

Reference yield:

: 65750-58-5
bis(p-nitrobenzyl) ketomalonate

: 65750-54-1
(4S,5R,6R)-4-Bromo-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]heptane-2,2-dicarboxylic acid bis-(4-nitro-benzyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1: 26 percent / tetrahydrofuran; toluene / 2.5 h / Heating

2: SOCl₂/pyridine / tetrahydrofuran / 1.) 5 min, -20 deg C; 2.) 0.5 h, 0 deg C; 3.) 1 h, 25 deg C

3: 57 percent / Bu₃P, K₂HPO₄ / dimethylformamide; H₂O / 0.58 h

4: 1.) Br₂ ; 2.) Et₃N / 1.) pentane, THF/ether, 15 min, 0 deg C; 2.) DMF, 2 h, r.t.

With pyridine; dipotassium hydrogenphosphate; thionyl chloride; tributylphosphine; bromine; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo01294a044