Boc-His(Trt)-OH

Base Information

• Chemical Name: Boc-His(Trt)-OH
• CAS No.: 32926-43-5
• Molecular Formula: C30H31N3O4
• Molecular Weight: 497.594
• Hs Code.: 29224999
• European Community (EC) Number: 685-644-6
• UNII: C9YH4KHR73
• Nikkaji Number: J3.560.619J
• Mol file: 32926-43-5.mol

Synonyms:Boc-His(Trt)-OH;32926-43-5;(S)-2-((tert-Butoxycarbonyl)amino)-3-(1-trityl-1H-imidazol-4-yl)propanoic acid;L-Histidine, N-[(1,1-dimethylethoxy)carbonyl]-1-(triphenylmethyl)-;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-tritylimidazol-4-yl)propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanoic acid;MFCD00153307;(S)-2-[(tert-Butoxycarbonyl)amino]-3-(1-trityl-1H-imidazol-4-yl)propanoic acid;C30H31N3O4;(2S)-2-[[(tert-Butoxy)carbonyl]amino]-3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanoic acid;C9YH4KHR73;SCHEMBL9959535;OYXZPXVCRAAKCM-SANMLTNESA-N;N-|A-Boc-N-im-trityl-L-histidine;Nalpha-Boc-N(im)-trityl-L-histidine;AKOS015903518;AM81820;CS-W011504;DS-2286;FD21670;HY-W010788;Boc-His(Trt)-OH, >=98.0% (TLC);Na-(tert-Butoxycarbonyl)-Nt-trityl-L-histidine;EN300-1589957;Q-101821;N-alpha-t-Butyloxycarbonyl-N-im-t-trityl-L-histidine;N-[(1,1-Dimethylethoxy)carbonyl]-1-(triphenylmethyl)-L-histidine;(S)-2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazol-4-yl)propanoic acid;2-((TERT-BUTOXYCARBONYL)AMINO)-3-(1-TRITYL-1H-IMIDAZOL-4-YL)PROPANOIC ACID

Chemical Property of Boc-His(Trt)-OH

Chemical Property:

• Vapor Pressure: 9.93E-19mmHg at 25°C
• Melting Point: ~130 °C (dec.)
• Refractive Index: 1.594
• Boiling Point: 667.5 °C at 760 mmHg
• PKA: 3.17±0.10(Predicted)
• Flash Point: 357.5 °C
• PSA: 93.45000
• Density: 1.16 g/cm³
• LogP: 5.63460
• Storage Temp.: Store at 0°C
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 497.23145648
• Heavy Atom Count: 37
• Complexity: 703

Purity/Quality:

≥98%, ^*data from raw suppliers

Boc-His(Trt)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CN(C=N1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CN(C=N1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)O
• Uses: Boc-His(Trt)-OH was used in the study to prepare and study structure-activity relationship of amino acid amides as selective inhibitors for dipeptidyl peptidases.

Technology Process of Boc-His(Trt)-OH

There total 20 articles about Boc-His(Trt)-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-amino-3-(N-tritylimidazolyl)propionic acid (35146-32-8,199119-46-5) → Nα-(tert-butyloxy)carbonyl-Nim-triphenylmethyl-L-histidine (32926-43-5,393568-74-6)

Guidance literature:

With potassium carbonate; In isopropyl alcohol; at 30 - 35 ℃; for 0.666667h;

DOI:10.1007/BF00580461

Reference yield: 85.0%

Nα-(tert-butyloxy)carbonyl-Nim-triphenylmethyl-L-histidine methyl ester (62697-87-4) → Nα-(tert-butyloxy)carbonyl-Nim-triphenylmethyl-L-histidine (32926-43-5,393568-74-6)

Guidance literature:

With lithium hydroxide; In methanol; at 4 ℃; for 2h;

DOI:10.1016/0968-0896(95)00183-2

Reference yield:

N-(tert-butoxycarbonyl)-L-histidine (17791-52-5) → Nα-(tert-butyloxy)carbonyl-Nim-triphenylmethyl-L-histidine (32926-43-5,393568-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile; CHCl₃ / 0.5 h

2: 2.) methanol / 1.) 1 h; 2.) 15 min

With methanol; triethylamine; In chloroform; acetonitrile;

DOI:10.1007/BF00580461

upstream raw materials:

trityl chloride

N^α-Boc-L-histidine trimethylsilyl ester

bromo-triphenyl-methane

N-(tert-butoxycarbonyl)-L-histidine

Downstream raw materials:

[3-({2'-[2-((2S,3R)-2-{(2S,3S,4R)-4-[(S)-2-tert-Butoxycarbonylamino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-3-hydroxy-butyrylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium

N-α-tert-butyloxycarbonyl-N-im-trityl-L-histidine pentafluorophenyl ester

N^α-[(tert-butyloxy)carbonyl]-N^β-[3(S)-[4-amino-6-[[[1-(S)-(({4(S)-[({1(S)-[({2-[4'-({[3-(dimethylsulfonio)-1-propyl]amino}carbonyl)-2',4-bithiazol-2-yl]-1-ethyl}amino)carbonyl]-2(R)-hydroxy-1-propyl}amino)carbonyl]-3(S)-hydroxy-2(R)-pentyl}amin...

[3-({2'-[2-((2S,3R)-2-{(2S,3S,4R)-4-[(S)-2-Amino-3-(1-trityl-1H-imidazol-4-yl)-propionylamino]-3-hydroxy-2-methyl-pentanoylamino}-3-hydroxy-butyrylamino)-ethyl]-[2,4']bithiazolyl-4-carbonyl}-amino)-propyl]-dimethyl-sulfonium

Refernces

• 1、 Pozdnev, V. F.. "IMPROVED METHODS OF OBTAINING Nim-TRITYL-SUBSTITUTED HISTIDINE DERIVATIVES". . p. 322 - 327. Retrieved 2007/10/02.