35897-34-8

Basic information

• Product Name: N-BOC-L-Arginine hydrochloride
• Synonyms: N-TERT-BUTOXYCARBONYL-L-ARGININE;N-T-BOC-L-ARGININE;N-ALPHA-BOC-L-ARGININE HYDROCHLORIDE;NALPHA-(TERT-BUTOXYCARBONYL)-L-ARGININE HYDROCHLORIDE;NALPHA-(TERT-BUTOXYCARBONYL)-L-ARGININE;N-ALPHA-T-BOC-L-ARG;N-ALPHA-T-BUTOXYCARBONYL-L-ARGININE;n-boc-L-arginine hydrochloride
• CAS NO: 35897-34-8
• Molecular Formula: C₁₁H₂₂N₄O₄*ClH
• Molecular Weight: 310.78
• EINECS: 237-295-2
• Product Categories: Amino Acids;Arginine [Arg, R];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series;Amino hydrochloride
• Mol File: 35897-34-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 494 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: White/Powder
• Density: 1.28 g/cm³
• Vapor Pressure: 4.17E-11mmHg at 25°C
• Refractive Index: -8 ° (C=2, H2O)
• Storage Temp.: -15°C
• Solubility: Acetic Acid (Sparingly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: N-BOC-L-Arginine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-L-Arginine hydrochloride(35897-34-8)
• EPA Substance Registry System: N-BOC-L-Arginine hydrochloride(35897-34-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 35897-34-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

InChI:InChI=1/C11H22N4O4.ClH/c1-11(2,3)19-10(18)15-7(8(16)17)5-4-6-14-9(12)13;/h7H,4-6H2,1-3H3,(H,15,18)(H,16,17)(H4,12,13,14);1H/t7-;/m0./s1

Synthetic route

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + tert-butyl 4'-<(2-n-butyl-4-oxo-1,3,8-triazaspiro<4.5>dec-1-en-3-yl)methyl>biphenyl-2-carboxylate (138401-29-3) → tert-butyl 4'-<<2-n-butyl-4-oxo-8--1,3,8-triazaspiro<4.5>dec-1-en-3-yl>methyl>biphenyl-2-carboxylate hydrochloride

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 18h;	95%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + 4-nitro-aniline (100-01-6) → N-(t-butoxycarbonyl)-L-arginine p-nitroanilide hydrochloride (99306-64-6)

Conditions	Yield
With pyridine; trichlorophosphate at -15℃;	91%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl chloride (154445-78-0) → (S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid

Conditions	Yield
With sodium hydroxide In water; acetone at 5℃; for 1h; Temperature;	82%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + N,N'-bis(4-nitrophenyl)phospheneimidous amide (134393-23-0) → N-(t-butoxycarbonyl)-L-arginine p-nitroanilide hydrochloride (99306-64-6)

Conditions	Yield
With pyridine at 40℃; for 4h;	75%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + obeticholic acid → C38H68N8O6

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	72.3%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + obeticholic acid → C32H56N4O5

Conditions	Yield
Stage #1: obeticholic acid With sodium hydride In tetrahydrofuran for 2h; Stage #2: Nα-t-butoxycarbonyl-arginine hydrochloride With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	71.4%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + benzyl chloroformate (501-53-1) → N7-<(benzyloxy)carbonyl>-N2-<(tert-butoxy)carbonyl>-L-arginine (51219-18-2)

Conditions	Yield
With sodium hydroxide	70%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + D-phenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester hydrochloride (128719-07-3) → N-tert-butoxycarbonyl-L-arginyl-D-phenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester (128719-16-4)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;	60.2%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + 5-(4-aminophenyl)-10,15,20-triphenylporphyrin (67605-64-5) → Nα-Boc-Arg-NH-TPP hydrochloride

Conditions	Yield
With pyridine; dmap; phosphorus trichloride at -15℃; for 1h; Condensation;	56%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + (S)-2-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester; hydrochloride (68762-02-7) → N-tert-butoxycarbonyl-L-arginyl(HCl)-D-tryptophyl-L-leucine methyl ester (128719-64-2)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 4℃;	54%

perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate (50903-47-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7) + acetic acid (64-19-7) → Boc-Gly-Pro-Arg-Gly-Gly-OH acetate

Conditions	Yield
Multistep reaction;	36%

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Ala-D-Trp-Phe-D-Pro-Pro-OMe hydrochloride (141663-87-8) → Boc-Arg-Ala-D-Trp-Phe-D-Pro-Pro-OMe

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 10 min, 2.) DMF, 20 deg C, 2 h; Yield given. Multistep reaction;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-Ala-D-Trp-Phe-D-Pro-Pro-NHMe hydrochloride (141636-75-1) → Boc-Arg-Ala-D-Trp-Phe-D-Pro-Pro-NMe (141636-53-5)

Conditions	Yield
With triethylamine; dicyclohexyl-carbodiimide 1.) DMF, 10 min, 2.) DMF, 20 deg C, 2 h; Yield given. Multistep reaction;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + {(S)-2-[(S)-2-((S)-2-Amino-6-benzyloxycarbonylamino-hexanoylamino)-3-methyl-butyrylamino]-4-methyl-pentanoylamino}-acetic acid methyl ester; compound with trifluoro-acetic acid (94770-24-8) → Boc-Arg(HCl)-Lys(Z)-Val-Leu-Gly-OCH3 (105220-35-7)

Conditions	Yield
With N-ethylmorpholine;; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h; pH=7; Yield given;

tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate (3392-07-2) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7) → Nα-tert-butoxycarbonylglycylprolylarginylglycylglycine

Conditions	Yield
Yield given. Multistep reaction;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Pro-Lys(Boc)-Pro-OMe (69355-83-5) → Boc-Arg-Pro-Lys(Boc)-Pro-OMe (82565-76-2)

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 8℃; for 19h; Yield given;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + (R)-N-(4-Aminomethyl-phenyl)-2-(N',N''-dicyclohexyl-guanidino)-3-naphthalen-2-yl-propionamide (195716-40-6) → ((S)-1-{4-[(R)-2-(N',N''-Dicyclohexyl-guanidino)-3-naphthalen-2-yl-propionylamino]-benzylcarbamoyl}-4-guanidino-butyl)-carbamic acid tert-butyl ester (195717-52-3)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide

n-Dodecylamine (124-22-1) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → ((S)-1-Dodecylcarbamoyl-4-guanidino-butyl)-carbamic acid tert-butyl ester; hydrochloride

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine 1) DMF, 25 deg C, 30 min; 2) DMF, 25 deg C, overnight; Yield given. Multistep reaction;

tetradecylamine (2016-42-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → ((S)-4-Guanidino-1-tetradecylcarbamoyl-butyl)-carbamic acid tert-butyl ester; hydrochloride

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine 1) DMF, 25 deg C, 30 min; 2) DMF, 25 deg C, overnight; Yield given. Multistep reaction;

hexadecylamine (143-27-1) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → ((S)-4-Guanidino-1-hexadecylcarbamoyl-butyl)-carbamic acid tert-butyl ester; hydrochloride

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine 1) DMF, 25 deg C, 30 min; 2) DMF, 25 deg C, overnight; Yield given. Multistep reaction;

1-aminodecane (2016-57-1) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → ((S)-1-Decylcarbamoyl-4-guanidino-butyl)-carbamic acid tert-butyl ester; hydrochloride

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine 1) DMF, 25 deg C, 30 min; 2) DMF, 25 deg C, overnight; Yield given. Multistep reaction;

chloro-trimethyl-silane (75-77-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → C14H30N4O4Si

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 1.5h; silylation;

N-tert-butoxycarbonyl-L-leucine (13139-15-6) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (S)-2-tert-Butoxycarbonylamino-3-[4-(diphenyl-phosphinoyloxy)-phenyl]-propionic acid (128797-22-8) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-Gly-OH, Boc-Lys(Fmoc)-OH, Boc-Pro-OH, Boc-Lys(Fmoc)-Pac-resin → alpha-Neoendorphin (Porcine) (77739-20-9)

Conditions	Yield
Yield given. Multistep reaction;

perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate (50903-47-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7) + Boc-Gly-ONSu → Nα-tert-butoxycarbonylglycylprolylarginylglycylglycine

Conditions	Yield
Yield given. Multistep reaction;

perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate (50903-47-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine pentafluorophenyl ester (50903-54-3) + Boc-Arg(Bzl)-OPfp 2 Boc-Pro-OPfp → H-Arg-Pro-Pro-Gly-Phe-Ser(OBzl)-Phe-Arg-Gly-Gly trihydrobromide

Conditions	Yield
Multistep reaction;

methanol (67-56-1) + perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate (50903-47-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester (3392-10-7) + protohemin IX 6(7)-mono-N-succinimide ester → Nα-[6-(protohemin IX)-yl]-Gly-Pro-Arg-Gly-Gly-OMe

Conditions	Yield
Multistep reaction;

methanol (67-56-1) + perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate (50903-47-4) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + Boc-glycine cesium salt (42538-64-7) + N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine pentafluorophenyl ester (50903-54-3) + Boc-Arg(Bzl)-OPfp 2 Boc-Pro-OPfpprotohemin IX → Nα-[6-(protohemin IX)-yl]-Arg-Pro-Pro-Gly-Phe-Ser(Bzl)-Phe-Arg-Gly-Gly-OMe

Conditions	Yield
Multistep reaction;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + isobutyl chloroformate (17462-58-7) → C12H21ClN4O5

Conditions	Yield
In N,N-dimethyl-formamide at -10℃; Anhydride formation;

Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) + glycerol (56-81-5) → rac-1-O-(Nα-tert-butoxycarbonyl-L-argininyl)glycerol hydrochloride + rac-2-O-(Nα-Boc-L-arginyl)glycerol hydrochloride

Conditions	Yield
With DL-dithiothreitol; papain In various solvent(s) at 50℃; for 24h; Title compound not separated from byproducts.;

[1]naphthylmethyl-[2]naphthylmethyl-amine (47292-14-8) + Nα-t-butoxycarbonyl-arginine hydrochloride (35897-34-8) → [4-guanidino-1-(naphthalen-2-ylmethyl-naphthalen-1-ylmethyl-carbamoyl)-butyl]-carbamic acid tert-butyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In N,N-dimethyl-formamide for 20h;

Downstream Products

• 99306-64-6 N-(t-butoxycarbonyl)-L-arginine p-nitroanilide hydrochloride 
• 186698-61-3 (S)-2-(tert-butoxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid 
• 81344-50-5 Arg(Z)>*HCl 
• 51219-20-6 Boc-Arg(Z)> 
• 67508-55-8 N-benzoyl-L-isoleucyl-L-α-glutamylglycyl-N-(4-nitrophenyl)-L-argininamide methyl ester hydrochloride 
• 40127-11-5 L-arginine p-nitroanilide dihydrochloride 
• 51219-18-2 N⁷-<(benzyloxy)carbonyl>-N²-<(tert-butoxy)carbonyl>-L-arginine 
• 105220-35-7 Boc-Arg(HCl)-Lys(Z)-Val-Leu-Gly-OCH₃ 
• 141636-53-5 Boc-Arg-Ala-D-Trp-Phe-D-Pro-Pro-NMe 
• 128719-16-4 N-tert-butoxycarbonyl-L-arginyl-D-phenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester