57113-90-3

Basic information

• Product Name: BENZOIC ACID, 2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-NITRO-METHYL ESTER
• Synonyms: Methyl 2-[(tert-butoxycarbonyl)aMino]-3-nitroben;Methyl 2-(tert-Butoxycarbonylamino)-3-nitrobenzoate;METHYL-2-[(T-BOC)-AMINO]-3-NITROBENZOATE;METHYL 2-([(1,1-DIMETHYLETHOXY)CARBONYL]AMINO)-3-NITROBENZOATE;BENZOIC ACID, 2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-NITRO-METHYL ESTER;Methyl-2-(tert-butoxy carbonyl amino)-3-nitro benzoate;3-nitro-, methyl ester;Benzoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-
• CAS NO: 57113-90-3
• Molecular Formula: C₁₃H₁₆N₂O₆
• Molecular Weight: 296.28
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 57113-90-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 104.0 to 108.0 °C
• Boiling Point: 376.924 °C at 760 mmHg
• Flash Point: 181.758 °C
• Appearance: /
• Density: 1.298 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.566
• Solubility: Dichloromethane
• PKA: 11.96±0.70(Predicted)
• CAS DataBase Reference: BENZOIC ACID, 2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-NITRO-METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOIC ACID, 2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-NITRO-METHYL ESTER(57113-90-3)
• EPA Substance Registry System: BENZOIC ACID, 2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-NITRO-METHYL ESTER(57113-90-3)

Safety Data

• Hazardous Substances Data: 57113-90-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C13H16N2O6/c1-13(2,3)21-12(17)14-10-8(11(16)20-4)6-5-7-9(10)15(18)19/h5-7H,1-4H3,(H,14,17)

Synthetic route

methyl 2-carboxy-3-nitrobenzoate (21606-04-2) + triethylamine (121-44-8) + tert-butyl alcohol (75-65-0) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Stage #1: methyl 2-carboxy-3-nitrobenzoate; triethylamine With diphenyl phosphoryl azide In DMF (N,N-dimethyl-formamide) at 20 - 35℃; for 3h; Industry scale; Stage #2: tert-butyl alcohol In DMF (N,N-dimethyl-formamide) at 85 - 90℃; for 4 - 7h; Heating / reflux;	86.7%

methyl 2-carboxy-3-nitrobenzoate (21606-04-2) + tert-butyl alcohol (75-65-0) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Stage #1: methyl 2-carboxy-3-nitrobenzoate With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl-formamide at 20 - 31℃; Inert atmosphere; Stage #2: tert-butyl alcohol In N,N-dimethyl-formamide at 85 - 87℃; for 9h; Stage #3: With methanol at 50 - 55℃; for 3h;	72.5%

2-Azidocarbonyl-3-nitro-benzoic acid methyl ester (856414-36-3) + tert-butyl alcohol (75-65-0) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
for 1.5h; Heating; Yield given;
for 2h; Heating / reflux;

methyl 2-carboxy-3-nitrobenzoate (21606-04-2) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2, DMF / toluene / 0.5 h / Heating 2: NaN3 / acetone; H2O / 1 h 3: 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 2.5 h / 75 °C 2.1: sodium azide; tetrabutylammomium bromide / toluene / 4 h / -10 - -5 °C 2.2: 1 h / 80 - 85 °C View Scheme

acid chloride of 1-methylhydrogen-3-nitrophthalate (73833-13-3) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 / acetone; H2O / 1 h 2: 1.5 h / Heating View Scheme

3-nitrophthalic acid (603-11-2) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: concd. H2SO4 / methanol 2: SOCl2, DMF / toluene / 0.5 h / Heating 3: NaN3 / acetone; H2O / 1 h 4: 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 24.75 h / 20 - 65 °C 2.1: N,N-dimethyl-formamide; thionyl chloride / toluene / 2.5 h / 75 °C 3.1: sodium azide; tetrabutylammomium bromide / toluene / 4 h / -10 - -5 °C 3.2: 1 h / 80 - 85 °C View Scheme

acid chloride of 1-methylhydrogen-3-nitrophthalate (73833-13-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + tert-butyl alcohol (75-65-0) → methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3)

Conditions	Yield
Stage #1: acid chloride of 1-methylhydrogen-3-nitrophthalate; N,N-dimethyl-formamide With sodium azide; tetrabutylammomium bromide In toluene at -10 - -5℃; for 4h; Stage #2: tert-butyl alcohol In toluene at 80 - 85℃; for 1h;

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) + 1-bromomethyl-4-bromobenzene (589-15-1) → C20H21BrN2O6 (892505-87-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 10h; Heating / reflux;	92%

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) + 7-(bromomethyl)-5-oxo-5H-dibenzocycloheptene-10-carbonitrile (169270-61-5) → methyl 2-<(tert-butoxycarbonyl)<(11-cyano-5-oxo-5H-dibenzocyclohepten-3-yl)methyl>amino>-3-nitrobenzoate (169270-79-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Heating;	86%

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) + 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → methyl 2-amino>-3-nitrobenzoate (139481-38-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Heating;	85%
With potassium carbonate In acetonitrile at 80 - 85℃; for 5h; Heating / reflux; Industry scale;

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → Methyl 3-amino-2-[(tert-butoxycarbonyl)amino]benzoate (474708-09-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 5h;	82%

1-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole + methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (1307853-80-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 3h; Inert atmosphere; Reflux;	81%

1-benzyl-5-[4'-(bromomethyl)biphenyl-2-yl]-1H-tetrazole + methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (1307853-80-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 9h; Reflux; Inert atmosphere;	81%

5-[4'-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole (1307853-40-2) + methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (1307853-69-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Reflux; Inert atmosphere;	71.1%

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) + Methyl 4'-(bromomethyl)biphenyl-2-carboxylate (114772-38-2) → 4'-{[tert-Butoxycarbonyl-(2-methoxycarbonyl-6-nitro-phenyl)-amino]-methyl}-biphenyl-2-carboxylic acid methyl ester (150058-11-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Heating;

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) + 7-(bromomethyl)dibenzooxepin-10-carbonitrile (169270-73-9) → 2-[tert-Butoxycarbonyl-(11-cyano-dibenzo[b,f]oxepin-3-ylmethyl)-amino]-3-nitro-benzoic acid methyl ester (1028312-00-6)

Conditions	Yield
With potassium carbonate In acetonitrile for 4h; Heating;

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate (136304-78-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate; tetrabutylammomium bromide / toluene / 12 h / 80 - 85 °C 1.2: 3 h / Reflux 2.1: tin(ll) chloride / ethyl acetate / 1.5 h / Reflux 2.2: 4.5 h / -10 - 0 °C 2.3: 0.5 h / Reflux View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → ethyl 3-amino-2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>benzoate (136285-69-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 78 percent / ethanol / 1.5 h / Heating View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 3-amino-2-<<<2'-(methoxycarbonyl)biphenyl-4-yl>methyl>amino>benzoate (139481-37-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: K2CO3 / acetonitrile / 4 h / Heating 2: 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate (139481-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 1-<(2'-cyanobiphenyl-4-yl)methyl>-2,3-dihydro-2-oxo-1H-benzimidazole-7-carboxylate (139481-33-7)

Conditions

Yield

Multi-step reaction with 5 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 90 percent / pyridine / 3 h / Ambient temperature 5: 89 percent / NaOMe / methanol / 21 h / Heating View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-chloro-1-<(2'-cyanobiphenyl-4-yl)methyl>-1H-benzimidazole-7-carboxylate (139481-34-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 90 percent / pyridine / 3 h / Ambient temperature 5: 89 percent / NaOMe / methanol / 21 h / Heating 6: 34 percent / POCl3 / 8 h / Heating View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → ethyl 1-<(2'-cyanobiphenyl-4-yl)methyl>-2-methyl-1H-benzimidazole-7-carboxylate (136304-69-3)

Conditions

Yield

Multi-step reaction with 5 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 78 percent / ethanol / 1.5 h / Heating 5: 73 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → 1-<(2'-cyanobiphenyl-4-yl)methyl>-2-<(methylthio)methyl>-1H-benzimidazole-7-carboxylic acid

Conditions

Yield

Multi-step reaction with 7 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 78 percent / ethanol / 1.5 h / Heating 5: 76 percent / CH2Cl2 / 2 h / Ambient temperature 6: acetonitrile; H2O / 41 h / 80 °C 7: 1 N aq. NaOH / ethanol / 3 h / Heating View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → 3-(2'-Cyano-biphenyl-4-ylmethyl)-2-methoxy-3H-benzoimidazole-4-carboxylic acid methyl ester (139481-47-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 70 percent / acetic acid / 0.67 h / 80 - 90 °C View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → 3-(2'-Cyano-biphenyl-4-ylmethyl)-2-methylamino-3H-benzoimidazole-4-carboxylic acid methyl ester (139481-48-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: ethanol / 17 h / 50 °C 5: 1.) methyl iodide, 2.) HCl / 1.) EtOH, reflux, 24 h, 2.) EtOH, H2O View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → ethyl 1-<(2'-cyanobiphenyl-4-yl)methyl>-2-mercapto-1H-benzimidazole-7-carboxylate (139481-43-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 78 percent / ethanol / 1.5 h / Heating 5: 82 percent / ethanol / 8 h / Heating View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-<<<2'-(methoxycarbonyl)biphenyl-4-yl>methyl>amino>-3-nitrobenzoate (139481-36-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 4 h / Heating 2: 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → methyl 2-<<(2'-cyanobiphenyl-4-yl)methyl>amino>-3-<(methoxycarbonyl)amino>benzoate (139481-35-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: 90 percent / pyridine / 3 h / Ambient temperature View Scheme

methyl 2-(N-tert-butoxycarbonylamino)-3-nitrobenzoate (57113-90-3) → 2-[(2'-Cyano-biphenyl-4-ylmethyl)-amino]-3-(3-methyl-thioureido)-benzoic acid methyl ester (139481-31-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetonitrile / 4 h / Heating 2: 77 percent / 30percent ethanolic HCl / ethyl acetate / 1 h / Ambient temperature 3: 1.) FeCl3*6H2O, activated carbon, 2.) hydrazine monohydrate / 1.) MeOH, THF, reflux, 30 min, 2.) MeOH, THF, reflux, 14 h 4: ethanol / 17 h / 50 °C View Scheme

Upstream product

• 21606-04-2 methyl 2-carboxy-3-nitrobenzoate 
• 121-44-8 triethylamine 
• 75-65-0 tert-butyl alcohol 
• 73833-13-3 acid chloride of 1-methylhydrogen-3-nitrophthalate 
• 68-12-2 N,N-dimethyl-formamide 
• 603-11-2 3-nitrophthalic acid 
• 856414-36-3 2-Azidocarbonyl-3-nitro-benzoic acid methyl ester 

Downstream Products

• 1202261-17-3 methyl 2-[(tert-butoxycarbonyl)(4-methoxybutyl)amino]-3-nitrobenzoate 
• 145040-37-5 candesartan cilexetil 
• 139481-72-4 2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid 
• 139481-28-0 methyl 2-<<2'-cyanobiphenyl-4-yl)methyl>amino>-3-nitrobenzoate 
• 1215298-35-3 methyl 2-ethoxy-1-({2′-[1-(phenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl}methyl)-1H-benzimidazole-7-carboxylate 
• 1307853-85-5 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 1-({4-[2-(1-benzyl-1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-2-ethoxy-1H-1,3-benzodiazole-7-carboxylate 
• 1307853-71-9 methyl 2-[({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate 
• 1307853-72-0 methyl 2-[({2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate 
• 1215298-30-8 methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate 
• 1307853-81-1 methyl 2-[({2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate 
• 1307853-73-1 C₃₃H₃₀N₆O₄ 
• 1307853-80-0 methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate 
• 1307853-69-5 methyl 2-(N-tert-butoxycarbonyl-N-{(2'-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate 
• 474708-09-3 Methyl 3-amino-2-[(tert-butoxycarbonyl)amino]benzoate 

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