Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester

Base Information

• Chemical Name: Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester
• CAS No.: 474645-98-2
• Molecular Formula: C₁₀H₂₁NO₅S
• Molecular Weight: 267.346
• DSSTox Substance ID: DTXSID30457700
• Wikidata: Q82280649
• Mol file: 474645-98-2.mol

Synonyms:474645-98-2;Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester;[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butyl] methanesulfonate;N-tert-Butoxycarbonyl (R)-2-Aminobutan-1-ol Methanesulfonic Acid;SCHEMBL8230634;DTXSID30457700

Chemical Property of Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester

Chemical Property:

• PSA: 93.57000
• LogP: 2.55110
• Solubility.: Chloroform, Dimethylformamide, DMSO
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 267.11404394
• Heavy Atom Count: 17
• Complexity: 339

Purity/Quality:

98% ^*data from raw suppliers

N-tert-Butoxycarbonyl(R)-2-Aminobutan-1-olMethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(COS(=O)(=O)C)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC[C@H](COS(=O)(=O)C)NC(=O)OC(C)(C)C
• Uses: Torcetrapib intermediate.

Technology Process of Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester

There total 2 articles about Methanesulfonic acid (R)-2-tert-butoxycarbonylamino-butyl ester 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%

methanesulfonyl chloride (124-63-0) + tert-butyl (R)-(1-hydroxybutan-2-yl)carbamate (150736-71-3) → methanesulfonic acid (R)-2-tert-butoxycarbonylaminobutyl ester (474645-98-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/chem.201602884

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methanesulfonic acid (R)-2-tert-butoxycarbonylaminobutyl ester (474645-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / Ambient temperature

2: TEA / CH₂Cl₂ / Ambient temperature

With TEA; In tetrahydrofuran; dichloromethane;

Reference yield: 74.0%

sodium cyanide (773837-37-9) + methanesulfonic acid (R)-2-tert-butoxycarbonylaminobutyl ester (474645-98-2) → (R)-N-tert-butyloxycarbonyl-3-aminopentanenitrile (198493-28-6)

Guidance literature:

sodium cyanide; With tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 35 ℃; for 2.5h; Inert atmosphere;

methanesulfonic acid (R)-2-tert-butoxycarbonylaminobutyl ester; In N,N-dimethyl-formamide; at 35 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/op060013i

upstream raw materials:

methanesulfonyl chloride

tert-butyl (R)-(1-hydroxybutan-2-yl)carbamate

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-N-tert-butyloxycarbonyl-3-aminopentanenitrile

((R)-1-ethyl-3-oxo-propyl)-carbamic acid tert-butyl ester

Refernces

• 1、 -. "AMINO-ETHYL-AMINO-ARYL (AEAA) COMPOUNDS AND THEIR USE". Page/Page column 140-141. . Retrieved 2009/10/06.
• 2、 Toujas, Jean-Louis,Jost, Eric,Vaultier, Michel. "Synthesis of homochiral N-Boc-β-aminoaldehydes from N-Boc-β-aminonitriles". . p. 713 - 718. Retrieved 2007/10/03.