(S)-2-Amino-6-hydroxyhexanoic acid

Base Information

• Chemical Name: (S)-2-Amino-6-hydroxyhexanoic acid
• CAS No.: 305-77-1
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• UNII: 874D12O72W
• Nikkaji Number: J977.779B
• Wikidata: Q27096308
• ChEMBL ID: CHEMBL1233976
• Mol file: 305-77-1.mol

Synonyms:2-amino-6-hydroxycaproic acid;6-hydroxy-2-aminocaproic acid;alpha-amino-epsilon-hydroxycaproic acid;epsilon-hydroxynorleucine;epsilon-hydroxynorleucine, (DL)-isomer;epsilon-hydroxynorleucine, (L)-isomer;HACA cpd

Chemical Property of (S)-2-Amino-6-hydroxyhexanoic acid

Chemical Property:

• Melting Point: 245-262 °C
• Boiling Point: 361.7°Cat760mmHg
• PKA: 2.53±0.24(Predicted)
• Flash Point: 172.6°C
• PSA: 83.55000
• Density: 1.189g/cm³
• LogP: 0.26120
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

98%min ^*data from raw suppliers

DL-6-Hydroxy norleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCO)CC(C(=O)O)N
• Isomeric SMILES: C(CCO)C[C@@H](C(=O)O)N
• Uses: An intermediate for antiviral and antihypertensive drugs An intermediate for antiviral and antihypertensive drugs.

Technology Process of (S)-2-Amino-6-hydroxyhexanoic acid

There total 1 articles about (S)-2-Amino-6-hydroxyhexanoic 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: 76.0%

rac-6-hydroxynorleucine (5462-80-6) → L-ε-hydroxynorleucine (305-77-1,5462-80-6,6033-32-5,16509-61-8)

Guidance literature:

DOI:10.1021/jo00326a061

Reference yield: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + L-ε-hydroxynorleucine (305-77-1,5462-80-6,6033-32-5,16509-61-8) → α-N-(tert-butoxycarbonyl)-L-ε-hydroxynorleucine (77611-37-1,81505-64-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; Ambient temperature; overnight;

DOI:10.1021/jo00326a061

Reference yield:

L-ε-hydroxynorleucine (305-77-1,5462-80-6,6033-32-5,16509-61-8) → (1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester (77611-38-2,84063-93-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / tetrahydrofuran; H₂O / Ambient temperature; overnight

2: 80 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide / H₂O / 0.5 h / Ambient temperature; pH 4.5

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; water;

DOI:10.1021/jo00326a061

upstream raw materials:

rac-6-hydroxynorleucine

Downstream raw materials:

α-N-(tert-butoxycarbonyl)-L-ε-hydroxynorleucine

(1-Benzyloxycarbamoyl-5-hydroxy-pentyl)-carbamic acid tert-butyl ester

Refernces