(S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one

Base Information

• Chemical Name: (S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one
• CAS No.: 139264-15-6
• Molecular Formula: C14H17N3O2
• Molecular Weight: 259.308
• UNII: 3FM32M4RD3
• Nikkaji Number: J694.107I
• Mol file: 139264-15-6.mol

Synonyms:139264-15-6;3FM32M4RD3;(S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one;(4S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)-1,3-oxazolidin-2-one;2-Oxazolidinone, 4-((3-(2-aminoethyl)-1H-indol-5-yl)methyl)-, (4S)-;2-Oxazolidinone, 4-((3-(2-aminoethyl)-1H-indol-5-yl)methyl)-, (S)-;2-Oxazolidinone, 4-[[3-(2-aminoethyl)-1H-indol-5-yl]methyl]-, (4S)-;Didesmethyl Zolmitriptan (90%);UNII-3FM32M4RD3;Zolmitriptan impurity D [EP];SCHEMBL5528416;AKOS030241072;ZOLMITRIPTAN IMPURITY D [EP IMPURITY];(4S)-4beta-[[3-(2-Aminoethyl)-1H-indol-5-yl]methyl]oxazolidin-2-one

Chemical Property of (S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one

Chemical Property:

• Vapor Pressure: 4E-14mmHg at 25°C
• Melting Point: 250 °C (decomp)
• Boiling Point: 595oC at 760 mmHg
• PKA: 12.57±0.40(Predicted)
• Flash Point: 313.6oC
• PSA: 83.63000
• Density: 1.299g/cm3
• LogP: 1.66030
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 259.132076794
• Heavy Atom Count: 19
• Complexity: 337

Purity/Quality:

97% ^*data from raw suppliers

DidesmethylZolmitriptan(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)CC2=CC3=C(C=C2)NC=C3CCN
• Isomeric SMILES: C1[C@@H](NC(=O)O1)CC2=CC3=C(C=C2)NC=C3CCN
• Uses: A metabolite of Zolmitriptan (Z639000).

Technology Process of (S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one

There total 10 articles about (S)-4-((3-(2-Aminoethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one 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: 60.0%

4-aminobutyrylaldehyde diethylacetal (6346-09-4) + (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one (187975-62-8,171550-12-2) → (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine (139264-15-6)

Guidance literature:

4-aminobutyrylaldehyde diethylacetal; (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one; With hydrogenchloride; In water; at 90 ℃; for 1h;

With sodium hydroxide; In water; pH=7;

Reference yield: 41.5%

ethyl (S)-3-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate (868622-21-3) → (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine (139264-15-6)

Guidance literature:

ethyl (S)-3-[2-(1,3-dioxoisoindolin-2-yl)ethyl]-5-[(2-oxooxazolidin-4-yl)methyl]-1H-indole-2-carboxylate; With water; potassium carbonate; for 2h; Heating / reflux;

With hydrogenchloride; In water; at 20 ℃; for 5h; pH=2; Heating / reflux;

With sodium hydroxide; In water; pH=10 - 11;

Reference yield:

4-nitro-3-phenyl-L-alanine (949-99-5) → (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine (139264-15-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / SOCl₂ / Ambient temperature

2: 46 percent / sodium borohydride / ethanol; H₂O / 2.5 h / Heating

3: 36 percent / aq. KOH / toluene / 1 h / 0 °C

4: 97 percent / H₂, aq. 2 N HCl / 10percent Pd/C / ethanol; ethyl acetate

5: 1.) aq. HCl, NaNO₂, 2.) SnCl₂ / 1.) from -5 deg C to 0 deg C, 30 min, 2.) RT, 3 h

6: 0.21 g / ethanol; H₂O / 2 h / Heating

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; thionyl chloride; hydrogen; tin(ll) chloride; sodium nitrite; palladium on activated charcoal; In ethanol; water; ethyl acetate; toluene;

DOI:10.1021/jm00018a016

upstream raw materials:

4-chlorobutanal dimethyl acetal

(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride

4-nitro-3-phenyl-L-alanine

(S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol

Downstream raw materials:

zolmitriptan

Refernces

• 1、 -. "Process for preparing optically pure zolmitriptan". Page/Page column 9. . Retrieved 2010/02/14.
• 2、 -. "Indolyl tetrahydropyridines for treating migraine". . . Retrieved 2008/06/13.