N-Boc-D-leucine N'-methoxy-N'-methylamide

Base Information

• Chemical Name: N-Boc-D-leucine N'-methoxy-N'-methylamide
• CAS No.: 129603-01-6
• Molecular Formula: C₁₃H₂₆N₂O₄
• Molecular Weight: 274.36
• Mol file: 129603-01-6.mol

Synonyms:N-Boc-D-leucineN\'-methoxy-N\'-methylamide;(R)-tert-butyl 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-yl carbamate;(R)-tert-butyl 1-(methoxy(methyl)amino)-4-methyl-1-oxopentan-2-ylcarbamate;N-Boc-D-Leu-N(CH3)OCH3;(R)-Nα-(tert-butoxycarbonyl)-N-methoxy-N-methylleucinamide;

Chemical Property of N-Boc-D-leucine N'-methoxy-N'-methylamide

Chemical Property:

• PSA: 67.87000
• LogP: 2.33650
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98.5% ^*data from raw suppliers

N-?[(1R)?-?1-?[(Methoxymethylamino?)?carbonyl]?-?3-?methylbutyl]?-carbamicAcid1,?1-?DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-?[(1R)?-?1-?[(Methoxymethylamino?)?carbonyl]?-?3-?methylbutyl]?-carbamic Acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing (R)-2-Amino-4-methyl-1-((S)-2-methyloxiran-2-yl)pentan-1-one Trifluoroacetate Salt (A605100), an impurity of carfilzomib (C183460). Carfilzomib is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Technology Process of N-Boc-D-leucine N'-methoxy-N'-methylamide

There total 2 articles about N-Boc-D-leucine N'-methoxy-N'-methylamide 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: 92.7%

N-Boc-D-Leu (16937-99-8,53296-34-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (R)-Nα-(tert-butoxycarbonyl)-N-methoxy-N-methylleucinamide (129603-01-6)

Guidance literature:

N-Boc-D-Leu; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 0.5h;

N,O-dimethylhydroxylamine*hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo402670d

Reference yield:

(R)-Boc-leucine hydrate (200937-21-9) + N,0-dimethylhydroxylamine (1117-97-1) → (R)-Nα-(tert-butoxycarbonyl)-N-methoxy-N-methylleucinamide (129603-01-6)

Guidance literature:

With 4-methyl-morpholine; isobutoxy chloroformate; Yield given. Multistep reaction; 1.) ethyl acetate, 15 min, ice bath, 2a.) 15 min, ice bath, 2b.) 20h, RT;

DOI:10.1055/s-1990-26900

Reference yield: 72.0%

(R)-Nα-(tert-butoxycarbonyl)-N-methoxy-N-methylleucinamide (129603-01-6) → (2R)-2-(1,1-dimethylethoxycarbonylamino)-4-methylpentanal (116662-96-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; or in diethyl ether;

DOI:10.1055/s-1990-26900

upstream raw materials:

(R)-Boc-leucine hydrate

N,0-dimethylhydroxylamine

N-Boc-D-Leu

N,O-dimethylhydroxylamine*hydrochloride

Downstream raw materials:

(2R)-2-(1,1-dimethylethoxycarbonylamino)-4-methylpentanal

tert-butoxycarbonyl-L-leucinal

(S)-2-methyl-4-aminononane hydrochloride

(R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-hydroxy-5-methylhexanoic acid

Refernces

• 1、 Said, Ahmed M.,Hangauer, David G.. "Binding cooperativity between a ligand carbonyl group and a hydrophobic side chain can be enhanced by additional H-bonds in a distance dependent manner: A case study with thrombin inhibitors". supporting information. p. 405 - 424. Retrieved 2015/05/05.
• 2、 Cai, Xiaoqing,Zaleski, Paul A.,Cagir, Ali,Hecht, Sidney M.. "Deglycobleomycin A6 analogues modified in the methylvalerate moiety". scheme or table. p. 3831 - 3844. Retrieved 2011/08/02.