(S)-2-(Tert-butoxycarbonylamino)non-8-enoic acid

Base Information

• Chemical Name: (S)-2-(Tert-butoxycarbonylamino)non-8-enoic acid
• CAS No.: 300831-21-4
• Molecular Formula: C14H25NO4
• Molecular Weight: 271.357
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID40467759
• Wikidata: Q82294826
• Mol file: 300831-21-4.mol

Synonyms:300831-21-4;(S)-2-(TERT-BUTOXYCARBONYLAMINO)NON-8-ENOIC ACID;(S)-2-((tert-Butoxycarbonyl)amino)non-8-enoic acid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]non-8-enoic Acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}non-8-enoic acid;8-Nonenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2S)-;(2S)-N-Boc-amino-non-8-enoic acid;MFCD03094930;SCHEMBL330005;DTXSID40467759;ZVCMWNFQYIQWSY-NSHDSACASA-N;BCP10536;CS-M1989;boc-(2s)-2-amino-8-nonenoic acid;AKOS022177182;(2S)-N-Boc-2-amino-non-8-enoic acid;(2S)-2-(Boc-amino)-non-8-enoic acid;AM805278;AS-39472;2(S)-tert-butoxycarbonylamino-8-nonenoic acid;(s)-2-(t-butoxycarbonylamino)-8-nonenoic acid;2(S)-tert-butoxycarbonylamino-non-8-enoic acid;(S)-2-(tertbutoxycarbonylamino)non-8-enoic acid;A876311;(2s)-2-[(t-butoxycarbonyl)amino]non-8-enoic acid;(S)-2-((tert-Butoxycarbonyl)amino)non-8-enoicacid;(2S)-2-[(tert-butoxycarbonyl)amino]non-8-enoic acid

Chemical Property of (S)-2-(Tert-butoxycarbonylamino)non-8-enoic acid

Chemical Property:

• Boiling Point: 422.7±45.0 °C(Predicted)
• PKA: 4.01±0.21(Predicted)
• PSA: 79.12000
• Density: 1.035±0.06 g/cm3(Predicted)
• LogP: 3.30520
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 271.17835828
• Heavy Atom Count: 19
• Complexity: 307

Purity/Quality:

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

(S)-2-((tert-Butoxycarbonyl)amino)non-8-enoicacid 97% ^*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(CCCCCC=C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCCCCC=C)C(=O)O

Technology Process of (S)-2-(Tert-butoxycarbonylamino)non-8-enoic acid

There total 19 articles about (S)-2-(Tert-butoxycarbonylamino)non-8-enoic acid 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: 97.0%

N-tert-butoxycarbonyl-2-amino-8-nonenoic acid dicyclohexylamine salt (1058705-94-4) → (S)-2-(tert-butoxycarbonylamino)non-8-enoic acid (300831-21-4)

Guidance literature:

With sodium hydroxide; In n-heptane; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b00418

Reference yield: 95.0%

ethyl (S)-((tert-butoxycarbonyl)amino)non-8-enoate (881683-81-4) → (S)-2-(tert-butoxycarbonylamino)non-8-enoic acid (300831-21-4)

Guidance literature:

ethyl (S)-((tert-butoxycarbonyl)amino)non-8-enoate; With methanol; lithium hydroxide; water;

With hydrogenchloride; pH=3 - 5;

Reference yield: 85.0%

(S)-2-amino-8-nonenoic acid (924307-76-6,1427467-46-6) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2-(tert-butoxycarbonylamino)non-8-enoic acid (300831-21-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; at 15 - 25 ℃; for 5h;

upstream raw materials:

di-tert-butyl dicarbonate

ethyl (S)-2-acetamido-8-nonenoate

[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-oct-7-enyl]-carbamic acid tert-butyl ester

(S)-4-Benzyl-3-non-8-enoyl-oxazolidin-2-one

Downstream raw materials:

(R)-2-{[(2S,4R)-1-((S)-2-tert-Butoxycarbonylamino-non-8-enoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-pent-4-enoic acid methyl ester

(S)-2-{[(2S,4R)-1-((S)-2-tert-Butoxycarbonylamino-non-8-enoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-pent-4-enoic acid methyl ester

(S)-2-tert-butoxycarbonylamino-8-nonenoic acid benzyl ester

(1R,2S)-ethyl 1-((2S,4R)-1-((S)-2-(((tert-butoxy)carbonyl)amino)non-8-enoyl)-4-hydroxypyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylate

Refernces

• 1、 Li, Hongmei,Scott, Jeremy P.,Chen, Cheng-Yi,Journet, Michel,Belyk, Kevin,Balsells, Jaume,Kosjek, Birgit,Baxter, Carl A.,Stewart, Gavin W.,Wise, Christopher,Alam, Mahbub,Song, Zhiguo Jake,Tan, Lushi. "Synthesis of bis-macrocyclic HCV protease inhibitor mk-6325 via intramolecular sp 2- sp 3 Suzuki-Miyaura coupling and ring closing metathesis". supporting information. p. 1533 - 1536. Retrieved 2015/03/30.
• 2、 -. "HEPATITIS C INHIBITOR COMPOUNDS". Page/Page column 64. . Retrieved 2011/06/23.