(2R)-2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate

Base Information

• Chemical Name: (2R)-2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate
• CAS No.: 4350-07-6
• Molecular Formula: C₁₁H₁₂N₂O₃
• Molecular Weight: 220.228
• Hs Code.: 2933990090
• Mol file: 4350-07-6.mol

Synonyms:

Chemical Property of (2R)-2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate

Chemical Property:

• Melting Point: 270C
• Boiling Point: 520.6±50.0 °C(Predicted)
• PKA: 2.22±0.10(Predicted)
• PSA: 99.34000
• Density: 1.484±0.06 g/cm3(Predicted)
• LogP: 1.52820
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 220.08479225
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

≥99.0% ^*data from raw suppliers

(R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21-20/21/22-36/37/38-65
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC2=C(C=C1O)C(=CN2)C[C@H](C(=O)[O-])[NH3+]

Technology Process of (2R)-2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate

There total 22 articles about (2R)-2-azaniumyl-3-(5-hydroxy-1H-indol-3-yl)propanoate 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:

N-methoxycarbonyl-4-cyano-D-2-aminobutyric acid methyl ester (93271-99-9) → 5-hydroxy-D-tryptophan (56-69-9,114-03-4,4350-07-6,4350-09-8,4298-20-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / Pb(OAc)2*H₂O, hydrogen / Raney nickel / acetic acid; H₂O / Ambient temperature

2: 61 percent / AcOH / H₂O / 2 h / 80 - 90 °C

3: 82 percent / 1 N NaOH / methanol / Ambient temperature

4: 100 percent / NaOH, hydrogen / 10percent Pd/C / H₂O / 2 h / Ambient temperature

5: Me₃SiI / CHCl₃ / 1 h / Heating

With sodium hydroxide; trimethylsilyl iodide; hydrogen; lead acetate; acetic acid; palladium on activated charcoal; nickel; In methanol; chloroform; water; acetic acid;

Reference yield:

(R)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid dimethyl ester (93271-96-6) → 5-hydroxy-D-tryptophan (56-69-9,114-03-4,4350-07-6,4350-09-8,4298-20-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / AcOH / H₂O / 2 h / 80 - 90 °C

2: 82 percent / 1 N NaOH / methanol / Ambient temperature

3: 100 percent / NaOH, hydrogen / 10percent Pd/C / H₂O / 2 h / Ambient temperature

4: Me₃SiI / CHCl₃ / 1 h / Heating

With sodium hydroxide; trimethylsilyl iodide; hydrogen; acetic acid; palladium on activated charcoal; In methanol; chloroform; water;

Reference yield:

N-methoxycarbonyl-D-glutamine methyl ester (93299-31-1) → 5-hydroxy-D-tryptophan (56-69-9,114-03-4,4350-07-6,4350-09-8,4298-20-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / p-toluenesulfonyl chloride / pyridine / 4 h / Ambient temperature

2: 69 percent / Pb(OAc)2*H₂O, hydrogen / Raney nickel / acetic acid; H₂O / Ambient temperature

3: 61 percent / AcOH / H₂O / 2 h / 80 - 90 °C

4: 82 percent / 1 N NaOH / methanol / Ambient temperature

5: 100 percent / NaOH, hydrogen / 10percent Pd/C / H₂O / 2 h / Ambient temperature

6: Me₃SiI / CHCl₃ / 1 h / Heating

With sodium hydroxide; trimethylsilyl iodide; hydrogen; lead acetate; acetic acid; p-toluenesulfonyl chloride; palladium on activated charcoal; nickel; In pyridine; methanol; chloroform; water; acetic acid;

upstream raw materials:

5-Benzyloxy-N^α-benzyloxycarbonyl-D-tryptophan

N-methoxycarbonyl-4-cyano-D-2-aminobutyric acid methyl ester

(R)-5-Hydroxy-pyrrolidine-1,2-dicarboxylic acid dimethyl ester

N-methoxycarbonyl-D-glutamine methyl ester

Downstream raw materials:

hyrtioerectine C

Refernces