Product Name

  • Name

    N-Boc-N'-nitro-L-arginine

  • EINECS 218-580-0
  • CAS No. 2188-18-3
  • Article Data15
  • CAS DataBase
  • Density 1.4 g/cm3
  • Solubility
  • Melting Point 257oC
  • Formula C11H21N5O6
  • Boiling Point
  • Molecular Weight 319.318
  • Flash Point
  • Transport Information
  • Appearance white crystal powder
  • Safety 26-36-37/39-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2188-18-3 (N-Boc-N'-nitro-L-arginine)
  • Hazard Symbols IrritantXi
  • Synonyms L-Ornithine,N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino(nitroamino)methyl]-;Ornithine,N2-carboxy-N5-(nitroamidino)-, N2-tert-butyl ester, L- (8CI);N2-tert-Butyloxycarbonyl-Nw-nitro-L-arginine;Na-tert-Butoxycarbonyl-NG-nitroarginine;Boc-Arg(NO2)-OH;
  • PSA 169.36000
  • LogP 1.84580

Synthetic route

N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sodium hydroxide; magnesium oxide In 1,4-dioxane; water for 24h; Ambient temperature;95%
With sodium hydroxide In 1,4-dioxane; water at 20 - 40℃; for 15h; pH=8.5;82%
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate
75844-68-7

tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane; water for 15h; Ambient temperature;82%
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

dimethylsulfonium methylsulfate

dimethylsulfonium methylsulfate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine In water Ambient temperature;78%
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
(i) Na2CO3, aq. dioxane, (ii) /BRN= 1363586/; Multistep reaction;
With magnesium oxide
With triethylamine In water; N,N-dimethyl-formamide
N-nitro-L-arginine
2149-70-4

N-nitro-L-arginine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine
t-butylpentachlorophenyl carbonate
18942-25-1

t-butylpentachlorophenyl carbonate

N-ω-nitro-L-arginine

N-ω-nitro-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With triethylamine In chloroform; N,N-dimethyl-formamide
t-butyloxycarbonyl-L-arginine
13726-76-6

t-butyloxycarbonyl-L-arginine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
With sulfuric acid; nitric acid Nitration;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / Et3N / acetonitrile / 5 h / 5 °C
2: 78 percent / Et3N / H2O / Ambient temperature
View Scheme
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine
175216-23-6

N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine

N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine
175216-24-7

N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; Acylation;100%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine
147081-44-5

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;99%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

methyl L-isoleucinate hydrochloride
18598-74-8

methyl L-isoleucinate hydrochloride

A

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

B

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester
102342-09-6

(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) ice bath, 1 h, 2.) 23 deg C, 15 h;A n/a
B 95%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl chloride
100-44-7

benzyl chloride

benzyl Nα-Boc-Nω-nitro-L-argininate
94770-45-3

benzyl Nα-Boc-Nω-nitro-L-argininate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 80℃; for 7h;95%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

tert-butyl L-alaninate hydrochloride
13404-22-3

tert-butyl L-alaninate hydrochloride

Boc-Arg(NO2)-Ala-OBu-t
107540-28-3

Boc-Arg(NO2)-Ala-OBu-t

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran 1.) -10 deg C, 1 h, 2.) room temp., 18 h;94%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl glycinate benzenesulfonate

benzyl glycinate benzenesulfonate

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
83103-21-3

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: benzyl glycinate benzenesulfonate With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
94%
tert-butyl (3R)3-aminopiperidine-1-carboxylate
188111-79-7

tert-butyl (3R)3-aminopiperidine-1-carboxylate

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;92%
2,3,4,5,6-pentafluorophenol
771-61-9

2,3,4,5,6-pentafluorophenol

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester
57866-90-7

Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0℃; for 12h;91%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester
147081-49-0

(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

(3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;91%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
16652-71-4

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

Boc-Arg(NO2)-Pro-OBzl
54046-53-6

Boc-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15℃; for 0.166667h;
Stage #2: With 1-hydroxybenzotriazol-hydrate In acetonitrile for 0.166667h; cooling;
Stage #3: benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride With 4-methyl-morpholine In N,N-dimethyl-formamide; acetonitrile at 20℃; pH=8;
90.5%
Stage #1: Boc-Arg(NO2)-OH With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15 - 0℃; for 0.166667h;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide; acetonitrile at -15℃; for 0.166667h;
Stage #3: benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride In N,N-dimethyl-formamide; acetonitrile at -15 - 20℃; pH=8;
88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Arg(NO2)-Ala-OBu-t
107540-29-4

H-Arg(NO2)-Ala-OBu-t

Boc-2-Ala-OBu-t
107540-30-7

Boc-2-Ala-OBu-t

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide 1.) -10 deg C, 1 h, 2.) room temp., 18 h;90%
H-Gly-Asp(OBzl)-Val-OBzl*HCl

H-Gly-Asp(OBzl)-Val-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn
350688-05-0

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Val-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
90%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Val-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
86%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C27H34N10O5

C27H34N10O5

Conditions
ConditionsYield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 20℃; for 5h;90%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride

H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride

Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl
423775-43-3

Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile89.2%
Stage #1: H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile at -15 - 0℃;
Stage #2: With benzotriazol-1-ol In N,N-dimethyl-formamide; acetonitrile at -15℃;
Stage #3: Boc-Arg(NO2)-OH In N,N-dimethyl-formamide; acetonitrile at -15 - 20℃; pH=8;
H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl

H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn
246516-47-2

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
89%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Ser(Bzl)-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide
139976-34-4

Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With N-methylcyclohexylamine; isobutyl chloroformate
Stage #2: N,0-dimethylhydroxylamine With N-methylcyclohexylamine
89%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Ala-Ser-OMe
107540-41-0

H-Ala-Ser-OMe

Boc-Arg(NO2)-Ala-Ser-OMe
107540-42-1

Boc-Arg(NO2)-Ala-Ser-OMe

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran 1.) -10 deg C, 1 h, 2.) room temp., 18 h;88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

Boc-Arg(Nω-NO2)-Gly-OCH3
111083-00-2

Boc-Arg(Nω-NO2)-Gly-OCH3

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; under 750.075 Torr; for 0.5h; Inert atmosphere;
Stage #2: glycine ethyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; under 750.075 Torr; pH=8.5; Inert atmosphere;
88%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: glycine ethyl ester hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; pH=8.5; Inert atmosphere;
88%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

1-(tert-butoxycarbonyl)-4-aminopiperidine
87120-72-7

1-(tert-butoxycarbonyl)-4-aminopiperidine

4-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

4-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

tert-butyl (3S)-3-aminopiperidine-1-carboxylate
625471-18-3

tert-butyl (3S)-3-aminopiperidine-1-carboxylate

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

(3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
H-Gly-Asp(OBzl)-Phe-OBzl*HCl

H-Gly-Asp(OBzl)-Phe-OBzl*HCl

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn
906673-81-2

Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: H-Gly-Asp(OBzl)-Phe-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 8h; pH=8.5; Further stages.;
87%
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: H-Gly-Asp(OBzl)-Phe-OBzl*HCl With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
87%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

glycine benzyl ester p-toluenesulfonic acid salt
1738-76-7

glycine benzyl ester p-toluenesulfonic acid salt

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
83103-21-3

Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: glycine benzyl ester p-toluenesulfonic acid salt With 4-methyl-morpholine In tetrahydrofuran at 0 - 20℃; for 10h; pH=9;
86%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile76%
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

H-Pro-OBzl
41324-66-7

H-Pro-OBzl

Boc-Arg(NO2)-Pro-OBzl
54046-53-6

Boc-Arg(NO2)-Pro-OBzl

Conditions
ConditionsYield
Stage #1: H-Pro-OBzl With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
86%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester
112208-06-7

Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester

Conditions
ConditionsYield
In methanol; benzene at 20℃; for 3h; Methylation;85%
In methanol; benzene
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Pro-Ala-Lys(Z)-OBzl hydrochloride

Pro-Ala-Lys(Z)-OBzl hydrochloride

Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
663954-94-7

Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.333333h; Cooling with ice;
Stage #2: Pro-Ala-Lys(Z)-OBzl hydrochloride With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
Stage #1: Pro-Ala-Lys(Z)-OBzl hydrochloride With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
77%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride

Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride

Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
713524-13-1

Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl

Conditions
ConditionsYield
Stage #1: Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 24h;
Stage #2: Boc-Arg(NO2)-OH With 4-methyl-morpholine In tetrahydrofuran at 20℃; for 24h;
85%
oxime resin

oxime resin

1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Boc-Orn(Z)-OH
2480-93-5

Boc-Orn(Z)-OH

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

cyclo[-Val-Orn(Z)-Leu-Arg(NO2)-D-Phe-Pro-Val-Orn(Z)-Leu-D-Phe-Pro-]

cyclo[-Val-Orn(Z)-Leu-Arg(NO2)-D-Phe-Pro-Val-Orn(Z)-Leu-D-Phe-Pro-]

Conditions
ConditionsYield
Stage #1: oxime resin; N-tert-butoxycarbonyl-L-leucine With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; solid phase reaction;
Stage #2: With trifluoroacetic acid In dichloromethane solid phase reaction;
Stage #3: 1-(tert-butoxycarbonyl)-L-proline; t-Boc-L-valine; N-tert-butoxycarbonyl-L-leucine; Boc-Arg(NO2)-OH; Boc-Orn(Z)-OH; Boc-D-Phe-OH Further stages;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

Pro-Gly-Pro benzyl ester trifluoroacetate

Pro-Gly-Pro benzyl ester trifluoroacetate

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.666667h;
Stage #2: Pro-Gly-Pro benzyl ester trifluoroacetate With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide for 72h;
85%
Boc-Arg(NO2)-OH
2188-18-3

Boc-Arg(NO2)-OH

TFA H-Pro-Gly-Pro-OBzl

TFA H-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions
ConditionsYield
Stage #1: Boc-Arg(NO2)-OH With dicyclohexyl-carbodiimide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.666667h;
Stage #2: TFA H-Pro-Gly-Pro-OBzl With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide for 72h;
85%

N-Boc-N'-nitro-L-arginine Specification

N-Boc-N'-nitro-L-arginine, its cas register number is 2188-18-3. It also can be called Boc-arg(n02)-oh; N-2-[(1,1-Dimethylethoxy)carbonyl]-n5-[imino(nitroamino)methyl]-l-ornithin; N-α-Boc-Nω-nitro-L-arginine; N-Alpha-t-Boc-n-omega-nitro-l-arginine; N-Alpha-t-Boc-n-g-nitro-l-arginine; N-Alpha-Tert-butyloxycarbonyl-n-gamma-nitro-l-arginine; N-Alpha-t-Butoxycarbonyl-n-g-nitro-l-arginine; N-Alpha-Tert-butoxycarbonyl-n-nitro-l-arginin. N-Boc-N'-nitro-L-arginine (CAS NO.2188-18-3) is a biochemical reagent used in the organic synthesis.

Physical properties about N-Boc-N'-nitro-L-arginine are: (1)ACD/LogP: 0.995; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -1.04; (4)ACD/LogD (pH 7.4): -2.58; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 11; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.564; (13)Molar Refractivity: 73.89 cm3; (14)Molar Volume: 227.1 cm3; (15)Polarizability: 29.29 10-24cm3; (16)Surface Tension: 55.3 dyne/cm; (17)Density: 1.4 g/cm3;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C11H21N5O6/c1-11(2,3)22-10(19)14-7(8(17)18)5-4-6-13-9(12)15-16(20)21/h7H,4-6H2,1-3H3,(H,14,19)(H,17,18)(H3,12,13,15)/t7-/m0/s1;
(2)InChIKey=OZSSOVRIEPAIMP-ZETCQYMHSA-N;
(3)SmilesO=C(OC(C)(C)C)N[C@H](C(=O)O)CCCNC(=N)N[N+](=O)[O-];

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