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
tert-butyl 2-oxo-1,3-oxazole-3(2H)-carboxylate
Boc-Arg(NO2)-OH
Conditions | Yield |
---|---|
With dmap; triethylamine In 1,4-dioxane; water for 15h; Ambient temperature; | 82% |
Conditions | Yield |
---|---|
With triethylamine In water Ambient temperature; | 78% |
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
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
Boc-Arg(NO2)-OH
Conditions | Yield |
---|---|
With triethylamine |
Conditions | Yield |
---|---|
With triethylamine In chloroform; N,N-dimethyl-formamide |
t-butyloxycarbonyl-L-arginine
Boc-Arg(NO2)-OH
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid Nitration; |
di-tert-butyl dicarbonate
Boc-Arg(NO2)-OH
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
N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine
N1-benzyloxycarbonyl-N8-(Nα-t-butoxycarbonyl-Ng-nitroarginyl-D-leucyl)-1,8-octanediamine
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
(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine
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
methyl L-isoleucinate hydrochloride
A
1,3-Dicyclohexylurea
B
(tert-butoxycarbonyl)-NG-nitroarginylisoleucyl methyl ester
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% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; sodium iodide In N,N-dimethyl-formamide at 80℃; for 7h; | 95% |
Boc-Arg(NO2)-OH
tert-butyl L-alaninate hydrochloride
Boc-Arg(NO2)-Ala-OBu-t
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
Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
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
Boc-Arg(NO2)-OH
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
Boc-Arg(NO2)-OH
Nα-tert-butoxycarbonyl-Nω-nitro-L-arginine pentafluorophenyl ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0℃; for 12h; | 91% |
Boc-Arg(NO2)-OH
(R)-3-aminopyrrolidine-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
benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride
Boc-Arg(NO2)-Pro-OBzl
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% |
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% |
Boc-Arg(NO2)-OH
Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Val-OBn
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
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
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
Boc-Arg(NO2)-Pro-Arg(NO2)-Pro-OBzl
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; |
Boc-Arg(NO2)-OH
Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Ser(Bn)-OBn
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
N,0-dimethylhydroxylamine
Nα-(tert-butoxycarbonyl)-L-nitroarginine N-methyl-O-methylcarboxamide
Conditions | Yield |
---|---|
Stage #1: Boc-Arg(NO2)-OH With N-methylcyclohexylamine; isobutyl chloroformate Stage #2: N,0-dimethylhydroxylamine With N-methylcyclohexylamine | 89% |
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
glycine ethyl ester hydrochloride
Boc-Arg(Nω-NO2)-Gly-OCH3
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
1-(tert-butoxycarbonyl)-4-aminopiperidine
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
tert-butyl (3S)-3-aminopiperidine-1-carboxylate
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
Boc-Arg(Nω-NO2)-Gly-Asp(OBn)-Phe-OBn
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
glycine benzyl ester p-toluenesulfonic acid salt
Nα-tert-butyloxycarbonyl-NG-nitroarginylglycine benzyl ester
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 |
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
diazomethyl-trimethyl-silane
Nα-(tert-butoxycarbonyl)-NG-nitro-L-arginine methyl ester
Conditions | Yield |
---|---|
In methanol; benzene at 20℃; for 3h; Methylation; | 85% |
In methanol; benzene |
Boc-Arg(NO2)-OH
Boc-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
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
Boc-Arg(NO2)-Arg(NO2)-Pro-Ala-Lys(Z)-OBzl
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% |
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
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% |
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% |
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% |
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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