tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate

Base Information

• Chemical Name: tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate
• CAS No.: 163210-89-7
• Molecular Formula: C₁₃H₂₄BrNO₄
• Molecular Weight: 338.242
• DSSTox Substance ID: DTXSID001135335
• Nikkaji Number: J975.832A
• Mol file: 163210-89-7.mol

Synonyms:163210-89-7;tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate;Butanoic acid, 4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]-,1,1-dimethylethyl ester, (2S)-;tert-butyl (2S)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;MFCD08275191;tert-Butyl (S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate;SCHEMBL13422140;KAHXNHVFTFWYDP-VIFPVBQESA-N;DTXSID001135335;Butanoic acid, 4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (2S)-;AC4629;AKOS032455854;AC-29765;CS-12371;(S)-tert-Butyl 4-bromo-2-((tert-butoxycarbonyl)amino)butanoate;(S)-tert-Butyl4-bromo-2-((tert-butoxycarbonyl)amino)butanoate;(2s)-4-bromo-2-(t-butoxycarbonylamino)-butanoic acid t-butyl ester;tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate (Boc-Abu(Br)-OtBu);1,1-Dimethylethyl (2S)-4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]butanoate

Chemical Property of tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 337.08887
• Heavy Atom Count: 19
• Complexity: 318

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-HAla(4-Br)-OtBu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCBr)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CCBr)NC(=O)OC(C)(C)C

Technology Process of tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate

There total 12 articles about tert-Butyl (S)-4-Bromo-2-(Boc-amino)butyrate 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: 83.67%

N-(tert-butyloxycarbonyl)-(S)-homoserine tert-butyl ester (81323-58-2) → tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate (163210-89-7)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.cclet.2021.03.055

Reference yield: 82.0%

N-tert-butoxycarbonyl aspartic acid tert-butyl ester (34582-32-6) → tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate (163210-89-7)

Guidance literature:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester; With N-methyl-2-indolinone; chloroformic acid ethyl ester;

With sodium tetrahydroborate; In methanol;

With carbon tetrabromide; triphenylphosphine;

DOI:10.1016/S0040-4039(03)01222-X

Reference yield: 80.0%

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]-4-bromobutanoate (163210-89-7)

Guidance literature:

With Bromotrichloromethane; dicyclohexyl-carbodiimide; 2-mercaptopyridine N-oxide; dmap; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Irradiation;

DOI:10.1016/S0968-0896(00)00324-2

upstream raw materials:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

1-tert-butyl 4-methyl (S)-2-{[(tert-butoxy)carbonyl]amino}butanedioate

Downstream raw materials:

Di-tert-butyl (5S)-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexane-dioate

tert-butyl 4-(N₄-benzyloxycarbonylcytosin-1-yl)-2S-butoxycarbonylaminobutyrate

tert-butyl 4-(N⁶-benzyloxycarbonyladenin-9-yl)-2S-butoxycarbonylaminobutyrate

tert-butyl 4-(N₃-benzoylthymin-1-yl)-2S-butoxycarbonylaminobutyrate

Refernces

• 1、 Wang, Tao,Kong, Yi-Fu,Xu, Yang,Fan, Jian,Xu, Hua-Jian,Bierer, Donald,Wang, Jun,Shi, Jing,Li, Yi-Ming. "Efficient synthesis of hydrocarbon-bridged diaminodiacids through nickel-catalyzed reductive cross-coupling". . p. 3970 - 3973. Retrieved 2017.
• 2、 Kang, Jie,Chen, Hong-Xue,Huang, Si-Qi,Zhang, Yun-Lai,Chang, Rong,Li, Fang-Yi,Li, Yan-Mei,Chen, Yong-Xiang. "Facile synthesis of Fmoc-protected phosphonate pSer mimetic and its application in assembling a substrate peptide of 14-3-3 ζ". . p. 2551 - 2553. Retrieved 2017.
• 3、 Bierer, Donald,Cui, Ji-Bin,Li, Yi-Ming,Shi, Jing,Wei, Xiao-Xiong,Zhao, Rui,Zhu, Huixia. "Chemical synthesis of disulfide surrogate peptides by using beta-carbon dimethyl modified diaminodiacids". supporting information. p. 9021 - 9025. Retrieved 2021/11/04.