6-[(Tert-butoxycarbonyl)amino]hexanoic acid

Base Information

• Chemical Name: 6-[(Tert-butoxycarbonyl)amino]hexanoic acid
• CAS No.: 6404-29-1
• Molecular Formula: C11H21 N O4
• Molecular Weight: 231.292
• Hs Code.: 2924199090
• European Community (EC) Number: 628-975-3
• DSSTox Substance ID: DTXSID50348464
• Nikkaji Number: J966.419J
• Wikidata: Q72448137
• Mol file: 6404-29-1.mol

Synonyms:6404-29-1;Boc-6-aminohexanoic acid;Boc-|A-Acp-OH;6-[(tert-butoxycarbonyl)amino]hexanoic acid;Boc-6-Aminocaproic acid;Boc-6-Ahx-OH;Boc-epsilon-Acp-OH;6-(Boc-amino)hexanoic acid;hexanoic acid, 6-[[(1,1-dimethylethoxy)carbonyl]amino]-;6-(Boc-amino)caproic acid;n-boc-6-aminohexanoic acid;6-((tert-Butoxycarbonyl)amino)hexanoic acid;6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;6-(tert-butoxycarbonylamino)hexanoic acid;MFCD00037798;6-{(tert-butoxycarbonyl)amino}hexanoic acid;Boc-epsilonAhx-OH;N-t-Butyloxycarbonyl-6-Amino-Hexanoic Acid;boc-E-acp-oh;Boc-epsilon-Ahx-OH;boc--aminocaproic acid;Boc-?-Acp-OH;Boc-Acp(6)-OH;Boc-|A- Aminocaproic acid;N-BOC-6-aminocaproic acid;t-Boc-6-aminohexanoic acid;6-(boc-amino)-caproic acid;Boc-NH-(CH2)5-COOH;N-Boc-6-amino hexanoic acid;N-Boc-6-amino-hexanoic acid;SCHEMBL345583;DTXSID50348464;6-t-butoxycarbonylaminohexanoic acid;STL466168;6-(1-t-butoxyformamido)hexanoic acid;Boc-Ahx-OH;6-(1-t-butyoxyformamido)hexanoic acid;6-(t-butoxycarbonyl)aminohexanoic acid;AKOS000169223;6-(t-Butoxycarbonylamino)hexanoic acid;AM82439;CS-W007529;HY-W007529;6-tert-butoxycarbonylamino-hexanoic acid;AC-24142;AS-19148;Boc-6-Ahx-OH, >=99.0% (T);BP-28245;n-t-butyloxycarbonyl-6-aminohexanoic acid;SY045493;6-(tert-butoxy-carbonylamino)hexanoic acid;N-t-Butoxycarbonyl-epsilon-aminocaproic acid;B4275;BB 0323039;FT-0664014;6-((tert-butoxycarbonyl)amino) hexanoic acid;EN300-30936;N-(tert-Butoxycarbonyl)-6-aminohexanoic Acid;6-{[(tert-butoxy)carbonyl]amino}hexanoic acid;I10802;A834623;J-300329;6-[[(1,1-Dimethylethoxy)carbonyl]amino]hexanoic acid;HEXANOIC ACID,6-AMINO,(N-TERT.BUTYLOXYCARBONYL);Z285919504

Chemical Property of 6-[(Tert-butoxycarbonyl)amino]hexanoic acid

Chemical Property:

• Vapor Pressure: 7.76E-07mmHg at 25°C
• Melting Point: 35-40 °C
• Boiling Point: 380.3oC at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 183.8oC
• PSA: 75.63000
• Density: 1.065g/cm3
• LogP: 2.54700
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Soluble in chloroform and ethyl acetate. Slightly soluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

tert-Butoxycarbonyl-ε-aminocaproicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCCCC(=O)O
• Description: Boc-6-aminohexanoic acid is an alkane chain with terminal carboxlic acid and Boc-protected amino groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs and other conjugation applications. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The Boc group can be deprotected under mild acidic conditions to form the free amine.
• Uses: 6-(Boc-amino)hexanoic acid is used in the preparation of esters of 6-aminohexanoic acid as antibacterial agents. EACA is reported to inhibit chymotrypsin, Factor VIIa, lysine carboxy peptidase, plasmin, and plasminogen activator. Protected ε-Aminocaproic Acid (A603015), Boc-6-AMinocaproic acid can be used in the preparatiom of esters of 6-aminohexanoic acid.

Technology Process of 6-[(Tert-butoxycarbonyl)amino]hexanoic acid

There total 21 articles about 6-[(Tert-butoxycarbonyl)amino]hexanoic 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: 100.0%

6-(Boc-amino)-1-hexanol (75937-12-1) → 6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1)

Guidance literature:

With 4-(polystyrylMeO)-2,2,6,6-tetraMepiperidin-1-yloxy radical; PS-CH₂Me₃(+)*ClO₂(-); PS-CH₂NMe₃(+)*H₂PO₄(-); potassium bromide; In water; acetonitrile; at 20 ℃; for 36h;

DOI:10.1039/b201776h

Reference yield: 97.0%

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + 6-aminohexanoic acid (60-32-2,93208-38-9) → 6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 20 ℃; for 23h; Inert atmosphere;

Reference yield: 97.0%

→ 6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1)

Guidance literature:

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

6-aminohexanoic acid

tert-Butyl 4-nitrophenyl carbonate

tert-butyldicarbonate

Downstream raw materials:

t-Boc-ε-caproic acid p-nitrophenyl ester

N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester

6-tert-Butoxycarbonylamino-hexanoic acid (8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

N-hydroxybenzotriazole ester of N-Boc-6-aminohexanoic acid

Refernces

• 1、 Sayyad, Nisar,Vrettos, Eirinaios I.,Karampelas, Theodoros,Chatzigiannis, Christos M.,Spyridaki, Katerina,Liapakis, George,Tamvakopoulos, Constantin,Tzakos, Andreas G.. "Development of bioactive gemcitabine-D-Lys6-GnRH prodrugs with linker-controllable drug release rate and enhanced biopharmaceutical profile". . p. 256 - 266. Retrieved 2019.
• 2、 Ryan, Philip,Shi, Yun,von Itzstein, Mark,Rudrawar, Santosh. "Novel bisubstrate uridine-peptide analogues bearing a pyrophosphate bioisostere as inhibitors of human O-GlcNAc transferase". . . Retrieved 2021/03/06.
• 3、 -. "TARGET PROTEIN EED DEGRADATION-INDUCING DEGRADUCER, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING DISEASES RELATED TO EED, EZH2, OR PRC2, COMPRISING SAME AS ACTIVE INGREDIENT". Paragraph 0378-0380. . Retrieved 2021/12/23.