(S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate

Base Information

• Chemical Name: (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate
• CAS No.: 234094-01-0
• Molecular Formula: C₁₀H₂₁N₃O₄
• Molecular Weight: 247.294
• European Community (EC) Number: 607-230-6
• DSSTox Substance ID: DTXSID901124595
• Nikkaji Number: J1.136.281H
• Mol file: 234094-01-0.mol

Synonyms:SCHEMBL14561000;AVRPVGHXWJUMRL-ZETCQYMHSA-N;DTXSID901124595;(S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate;1,1-Dimethylethyl N-[(1S)-2-[(2-aminoethyl)amino]-1-(hydroxymethyl)-2-oxoethyl]carbamate;234094-01-0

Chemical Property of (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 247.15320616
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CO)C(=O)NCCN
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CO)C(=O)NCCN

Technology Process of (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate

There total 2 articles about (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate 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: 75.0%

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + ethylenediamine (107-15-3,85404-18-8) → (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate (234094-01-0) + {1-[2-(2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-ethylcarbamoyl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester

Guidance literature:

In toluene; at 23.5 ℃; for 22.5h;

DOI:10.1080/00397919908086243

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + ethylenediamine (107-15-3,85404-18-8) → (S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate (234094-01-0)

Guidance literature:

di-tert-butyl dicarbonate; methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride; With triethylamine; In toluene; at 12 - 20 ℃; Large scale;

ethylenediamine; In toluene; at 20 - 26 ℃; Large scale;

Reference yield:

(S)-tert-butyl (1-((2-aminoethyl)amino)-3-hydroxy-1-oxopropan-2-yl)carbamate (234094-01-0) → ({(R)-1-({[2-(Bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino}-methyl)-2-[(4,4-diphenyl-cyclohexyloxy)-hydroxy-phosphoryloxy]-ethyl}-methyl-amino)-acetic acid

Guidance literature:

Multi-step reaction with 5 steps

1.1: 5.5 g / BH₃*THF / tetrahydrofuran / 168 h / 60 - 65 °C

2.1: 14.0 g / i-Pr₂NEt; KI / dimethylformamide / 24 h / 20 °C

3.1: imidazole / tetrahydrofuran / 0.33 h / 0 - 5 °C

3.2: hexane; tetrahydrofuran / 0.33 h / -5 - 0 °C

4.1: aq. NaIO₄ / hexane; tetrahydrofuran; toluene / 0.75 h / 5 - 20 °C

5.1: 0.385 g / aq. HCl / 16 h / 20 - 25 °C

With 1H-imidazole; hydrogenchloride; sodium periodate; borane-THF; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200500338

upstream raw materials:

N-tert-butyloxycarbonyl-L-serine methyl ester

ethylenediamine

di-tert-butyl dicarbonate

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

Downstream raw materials:

2,2’-((2-(((2R)-2-(bis(carboxymethyl)amino)-3-((((4,4-diphenylcyclohexyl)oxy)(hydroxy)phosphoryl)oxy)propyl)(carboxymethyl)amino)ethyl)azanediyl)diacetic acid

Refernces

• 1、 -. "PROCESS FOR MANUFACTURE OF GADOFOSVESET TRISODIUM MONOHYDRATE". Page/Page column 15; 16. . Retrieved 2014/10/15.