N(alpha), N-(im)-Di-Boc-L-histidine methyl ester

Base Information

• Chemical Name: N(alpha), N-(im)-Di-Boc-L-histidine methyl ester
• CAS No.: 17791-51-4
• Molecular Formula: C17H27 N3 O6
• Molecular Weight: 369.418
• DSSTox Substance ID: DTXSID50447860
• Nikkaji Number: J25.231J
• Wikidata: Q82266752
• Mol file: 17791-51-4.mol

Synonyms:17791-51-4;N(alpha), N-(im)-Di-Boc-L-histidine methyl ester;tert-butyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]imidazole-1-carboxylate;N(Alpha),n-(im)-di-boc-l-histidinemethylester;20898-43-5;Na,nim-bis-boc-L-histidine methyl ester;(S)-tert-Butyl 4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-imidazole-1-carboxylate;SCHEMBL3439706;DTXSID50447860;ZYCZFTGHOVFXLZ-LBPRGKRZSA-N;N,1-bis-BOC-histidine methyl ester;MFCD03094049;AKOS030627802;GS-5998;[Methyl(S)-3[1-(1,1-dimethylethoxycarbonyl)-1-H-imidazol-4-yl]-2-[(1,1-dimethylethoxycarbonyl)amino]propionate];H10608;N,1-bis-t-butoxycarbonyl-L-histidine methyl ester;J-011330;N-(alpha),N-(Im)-Di-Boc-L-histidine methyl ester;N( alpha ), N-(im)-Di-Boc-L-histidine methyl ester;N(alpha), N-(im)-Di-Boc-L-histidine methyl ester, 97%;(S)-tert-Butyl4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-imidazole-1-carboxylate;tert-butyl 4-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxy-3-oxopropyl]-1H-imidazole-1-carboxylate

Chemical Property of N(alpha), N-(im)-Di-Boc-L-histidine methyl ester

Chemical Property:

• Melting Point: 113-116 °C(lit.)
• Refractive Index: 1.516
• PSA: 112.24000
• Density: 1.17g/cm3
• LogP: 2.47950
• Storage Temp.: Store at 0-5°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 369.18998559
• Heavy Atom Count: 26
• Complexity: 524

Purity/Quality:

98%,99%, ^*data from raw suppliers

N(alpha),N-(IM)-Di-boc-L-histidinemethylester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CN(C=N1)C(=O)OC(C)(C)C)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CN(C=N1)C(=O)OC(C)(C)C)C(=O)OC

Technology Process of N(alpha), N-(im)-Di-Boc-L-histidine methyl ester

There total 5 articles about N(alpha), N-(im)-Di-Boc-L-histidine methyl ester 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: 70.0%

di-tert-butyl dicarbonate (24424-99-5) + L-histidine methyl ester (1499-46-3,10331-70-1,17720-12-6,62013-45-0) → methyl (S)-3-<1-(1,1-dimethylethoxycarbonyl)-1H-imidazol-5-yl>-2-<(1,1-dimethylethoxycarbonyl)amino>propionate (17791-51-4)

Guidance literature:

With 1-butyl-3-methylimidazolium trifluoroacetate; In neat (no solvent); at 20 ℃; for 0.0833333h; chemoselective reaction;

DOI:10.1039/c4ra02670e

Reference yield: 17.0%

di-tert-butyl dicarbonate (24424-99-5) + l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → methyl (S)-3-<1-(1,1-dimethylethoxycarbonyl)-1H-imidazol-5-yl>-2-<(1,1-dimethylethoxycarbonyl)amino>propionate (17791-51-4) + 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester (20898-43-5,133467-03-5,165062-56-6)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; for 1.5h; Ambient temperature;

DOI:10.1021/jo00125a014

Reference yield:

L-histidine (71-00-1) → methyl (S)-3-<1-(1,1-dimethylethoxycarbonyl)-1H-imidazol-5-yl>-2-<(1,1-dimethylethoxycarbonyl)amino>propionate (17791-51-4) + 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester (20898-43-5,133467-03-5,165062-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride

2: sodium hydrogencarbonate / tetrahydrofuran; water

With hydrogenchloride; sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1039/c2gc35367a

upstream raw materials:

di-tert-butyl dicarbonate

l-histidine methyl ester dihydrochloride

L-Histidine methyl ester

L-histidine

Downstream raw materials:

2-mercapto-L-histidine

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(1H-imidazol-4-yl)propanoate

Refernces

• 1、 Torikai, Kohei,Watanabe, Louis A.,Yanagimoto, Ryota. "N(?)-2-Naphthylmethoxymethyl-Protected Histidines: Scalable, Racemization-Free Building Blocks for Peptide Synthesis". . p. 448 - 453. Retrieved 2020/04/08.
• 2、 Lim, David,Gründemann, Dirk,Seebeck, Florian P.. "Total Synthesis and Functional Characterization of Selenoneine". supporting information. p. 15026 - 15030. Retrieved 2019/09/12.