2188-18-3

Basic information

• Product Name: N-Boc-N'-nitro-L-arginine
• Synonyms: boc-arg(n02)-oh;n2-[(1,1-dimethylethoxy)carbonyl]-n5-[imino(nitroamino)methyl]-l-ornithin;Nα-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-ARGININE
• CAS NO: 2188-18-3
• Molecular Formula: C₁₁H₂₁N₅O₆
• Molecular Weight: 319.31
• EINECS: 218-580-0
• Product Categories: Amino Acids;Amino Acid Derivatives;Arginine [Arg, R];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 2188-18-3.mol

Chemical Properties

• Melting Point: 111-113 °C
• Appearance: /Solid
• Density: 1.4 g/cm³
• Refractive Index: 1.564
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly, Heated)
• PKA: 3.84±0.50(Predicted)
• BRN: 2015163
• CAS DataBase Reference: N-Boc-N'-nitro-L-arginine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-nitro-L-arginine(2188-18-3)
• EPA Substance Registry System: N-Boc-N'-nitro-L-arginine(2188-18-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-67-19
• Safety Statements: 26-36-37/39-24/25
• WGK Germany: 1
• F: 10
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2188-18-3(Hazardous Substances Data)

Usage

Uses

Used in Peptide Chemistry:
N-Boc-N'-nitro-L-arginine is used as a protected amino acid for peptide synthesis. The Boc group serves as a temporary protecting group that prevents unwanted side reactions during the peptide assembly process. It is removed under mild acidic conditions once the desired peptide sequence is formed.
Used in Pharmaceutical Research:
N-Boc-N'-nitro-L-arginine is used as a nitric oxide (NO) synthase inhibitor for studying the effects of various compounds on nitric oxide production. Nitric oxide is a crucial signaling molecule involved in numerous physiological processes, including vasodilation, immune response, and neurotransmission. Inhibiting its production can help researchers understand the role of nitric oxide in various diseases and develop potential therapeutic strategies.
Used in Sepsis Treatment Research:
N-Boc-N'-nitro-L-arginine is used as a research tool to study the effects of methylene blue (MB) for the treatment of sepsis induced by bowel perforation. Sepsis is a life-threatening condition caused by the body's response to an infection, and understanding the underlying mechanisms can lead to the development of more effective treatments.

InChI:InChI=1/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-/m1/s1

Synthetic route

N-nitro-L-arginine (2149-70-4) + di-tert-butyl dicarbonate (24424-99-5) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
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) + tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate (75844-68-7) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
With dmap; triethylamine In 1,4-dioxane; water for 15h; Ambient temperature;	82%

N-nitro-L-arginine (2149-70-4) + dimethylsulfonium methylsulfate → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
With triethylamine In water Ambient temperature;	78%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + N-nitro-L-arginine (2149-70-4) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
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) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
With triethylamine

t-butylpentachlorophenyl carbonate (18942-25-1) + N-ω-nitro-L-arginine → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
With triethylamine In chloroform; N,N-dimethyl-formamide

t-butyloxycarbonyl-L-arginine (13726-76-6) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
With sulfuric acid; nitric acid Nitration;

di-tert-butyl dicarbonate (24424-99-5) → Boc-Arg(NO2)-OH (2188-18-3)

Conditions	Yield
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) + N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine (175216-23-6) → N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine (175216-24-7)

Conditions	Yield
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) + (3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine (147081-44-5) → (3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
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) + methyl L-isoleucinate hydrochloride (18598-74-8) → 1,3-Dicyclohexylurea (2387-23-7) + (tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester (102342-09-6)

Conditions	Yield
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) + benzyl chloride (100-44-7) → benzyl Nα-Boc-Nω-nitro-L-argininate (94770-45-3)

Conditions	Yield
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) + tert-butyl L-alaninate hydrochloride (13404-22-3) → Boc-Arg(NO2)-Ala-OBu-t (107540-28-3)

Conditions	Yield
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) + benzyl glycinate benzenesulfonate → Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester (83103-21-3)

Conditions	Yield
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) + Boc-Arg(NO2)-OH (2188-18-3) → (3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
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) + Boc-Arg(NO2)-OH (2188-18-3) → Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester (57866-90-7)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0℃; for 12h;	91%

Boc-Arg(NO2)-OH (2188-18-3) + (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester (147081-49-0) → (3R)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
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) + benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → Boc-Arg(NO2)-Pro-OBzl (54046-53-6)

Conditions	Yield
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) + H-Arg(NO2)-Ala-OBu-t (107540-29-4) → Boc-2-Ala-OBu-t (107540-30-7)

Conditions	Yield
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 + Boc-Arg(NO2)-OH (2188-18-3) → Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn (350688-05-0)

Conditions	Yield
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) + 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (152460-10-1) → C27H34N10O5

Conditions	Yield
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) + H-Pro-Arg(NO2)-Pro-OBzl monohydrochloride → Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl (423775-43-3)

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate In acetonitrile	89.2%
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 + Boc-Arg(NO2)-OH (2188-18-3) → Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn (246516-47-2)

Conditions	Yield
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) + N,0-dimethylhydroxylamine (1117-97-1) → Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide (139976-34-4)

Conditions	Yield
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) + H-Ala-Ser-OMe (107540-41-0) → Boc-Arg(NO2)-Ala-Ser-OMe (107540-42-1)

Conditions	Yield
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) + glycine ethyl ester hydrochloride (5680-79-5) → Boc-Arg(Nω-NO2)-Gly-OCH3 (111083-00-2)

Conditions	Yield
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) + 1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) → 4-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
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) + tert-butyl (3S)-3-aminopiperidine-1-carboxylate (625471-18-3) → (3S)-3-({(2S)-2-[(tert-butoxycarbonyl)amino]-5-(3-nitroguanidino)pentanoyl}amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
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 + Boc-Arg(NO2)-OH (2188-18-3) → Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn (906673-81-2)

Conditions	Yield
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) + glycine benzyl ester p-toluenesulfonic acid salt (1738-76-7) → Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester (83103-21-3)

Conditions	Yield
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 acetonitrile	76%
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide

Boc-Arg(NO2)-OH (2188-18-3) + H-Pro-OBzl (41324-66-7) → Boc-Arg(NO2)-Pro-OBzl (54046-53-6)

Conditions	Yield
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) + diazomethyl-trimethyl-silane (18107-18-1) → Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester (112208-06-7)

Conditions	Yield
In methanol; benzene at 20℃; for 3h; Methylation;	85%
In methanol; benzene

Boc-Arg(NO2)-OH (2188-18-3) + Pro-Ala-Lys(Z)-OBzl hydrochloride → Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl (663954-94-7)

Conditions	Yield
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) + Arg(NO2)-Pro-Ala-Lys(Z)-OBzl hydrochloride → Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl (713524-13-1)

Conditions	Yield
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 + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + t-Boc-L-valine (13734-41-3) + N-tert-butoxycarbonyl-L-leucine (13139-15-6) + Boc-Arg(NO2)-OH (2188-18-3) + Boc-Orn(Z)-OH (2480-93-5) + Boc-D-Phe-OH (18942-49-9) → cyclo[-Val-Orn(Z)-Leu-Arg(NO2)-D-Phe-Pro-Val-Orn(Z)-Leu-D-Phe-Pro-]

Conditions	Yield
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) + Pro-Gly-Pro benzyl ester trifluoroacetate → Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions	Yield
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) + TFA H-Pro-Gly-Pro-OBzl → Boc-Arg(NO2)-Pro-Gly-Pro-OBzl

Conditions	Yield
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%

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 2149-70-4 N-nitro-L-arginine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 18942-25-1 t-butylpentachlorophenyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 75844-68-7 tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate 
• 13726-76-6 t-butyloxycarbonyl-L-arginine 
• 2149-70-4 N^ω-nitro-L-arginine 
• 50739-44-1 1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate 

Downstream Products

• 14470-57-6 tert.-Butyloxycarbonyl-N^ω-nitro-ω-arginin-benzyloxycarbonyl-hydrazid 
• 2132-52-7 Boc-Arg(NO₂)-Ala-OBzl 
• 69129-24-4 C₂₄H₃₈N₆O₇ 
• 2149-70-4 N-nitro-L-arginine 
• 83103-21-3 N^α-tert-butyloxycarbonyl-N^G-nitroarginylglycine benzyl ester 
• 68455-62-9 Boc-Arg(NO₂)-Lys(Z)-OMe 
• 2387-23-7 1,3-Dicyclohexylurea 
• 102342-09-6 (tert-butoxycarbonyl)-N^G-nitroarginylisoleucyl methyl ester 
• 85642-21-3 N^α-tert-butoxycarbonyl-N^γ-nitro-L-arginyl-L-phenylalaninamide 
• 133463-26-0 Boc-Arg(NO₂)-Tyr-OMe 
• 79700-95-1 Boc-Arg(NO₂)-D-Glu(OBzl)NH₂ 
• 116084-64-1 Boc-Arg(NO₂)-Phe-Phe-Phe-OEt 

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A new biological active cyclic peptide (Nitro) Hymenamide A has been synthesized and the structure was established on the basis of analytical, IR, NMR and mass spectral data. The new compound was subjected to both antimicrobial and pharmacological studies.

3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxy-carbonylation and Benzyloxycarbonylation of Amino Groups

Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation.For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl and 3-benzyloxycarbonyl-2-oxazolones in aqueous solution at room temperature.A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivate, which failed to give polymeric compounds), and these were successfully used for amino protection as well.Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.Keywords - 3-alkoxycarbonyl-2-oxazolone; poly(2-alkoxycarbonyl-2-oxazolone); 3-tert-butoxycarbonyl-2-oxazolone; 3-benzyloxycarbonyl-2-oxazolone; amino protection

SYNTHESIS OF MESOIONIC TRIAZOLOPYRIDINE. III. APPLICATIONS OF N-ACYL MESOIONIC TRIAZOLOPYRIDINES AS ACYLATING REAGENTS.

Utility of N-acyl mesoionic triazolopyridines as acylating reagents was investigated concerning with peptide synthesis. Several dipeptides and N-alkoxycarbonyl amino acids were prepared by use of these reagents.