BOC-ALA-N(OCH3)CH3

Base Information

• Chemical Name: BOC-ALA-N(OCH3)CH3
• CAS No.: 87694-49-3
• Molecular Formula: C₁₀H₂₀N₂O₄
• Molecular Weight: 232.28
• Hs Code.: 2924199090
• Mol file: 87694-49-3.mol

Synonyms:Carbamicacid, [(1S)-2-(methoxymethylamino)-1-methyl-2-oxoethyl]-, 1,1-dimethylethylester (9CI);Carbamic acid, [2-(methoxymethylamino)-1-methyl-2-oxoethyl]-,1,1-dimethylethyl ester, (S)-;(S)-2-((tert-Butoxycarbonyl)amino)-N-methoxy-N-methylpropanamide;(S)-2-(tert-Butoxycarbonylamino)-N-methoxy-N-methylpropionamide;(S)-[1-(N-Methoxy-N-methylcarbamoyl)ethyl]carbamicacid tert-butyl ester;tert-Butyl(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethylcarbamate;tert-Butyl N-[(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl]carbamate;tert-Butyl N-[(S)-1-(N-methoxy-N-methylcarbamoyl)ethyl]carbamate;N-[(1S)-2-(Methoxymethylamino)-1-methyl-2-oxoethyl]-carbamic acid tert-butyl ester;

Chemical Property of BOC-ALA-N(OCH3)CH3

Chemical Property:

• Melting Point: 148-153 °C(lit.)
• PKA: 11.19±0.46(Predicted)
• PSA: 67.87000
• Density: 1.07 g/cm³
• LogP: 1.31030
• Storage Temp.: Store at 0°C
• Solubility.: soluble in Methanol

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-alanine N-methoxy-N-methyl amide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reduced by LiAlH4 to give the corresponding Boc-amino acid aldehyde.

Technology Process of BOC-ALA-N(OCH3)CH3

There total 13 articles about BOC-ALA-N(OCH3)CH3 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%

L-N-Boc-Ala (15761-38-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2,87694-49-3)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1002/anie.201303108

Reference yield: 95.0%

L-N-Boc-Ala (15761-38-3) + N,0-dimethylhydroxylamine (1117-97-1) → tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2,87694-49-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 81.0%

C39H39NO4P(1+)*ClO4(1-) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2,87694-49-3)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -20 ℃; for 1.5h;

upstream raw materials:

L-N-Boc-Ala

N,O-dimethylhydroxylamine*hydrochloride

N,0-dimethylhydroxylamine

[(1S)-2-imidazol-1-yl-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

(S)-tert-butyl (1-oxo-1-(p-tolyl)propan-2-yl)carbamate

(S)-1-methyl-N-(t-butoxycarbonyl)-2-propynamine

tert-butyl N-[(1S)-2-hydroxy-1-methylpropyl]carbamate

Boc-Ala-ψ-(CH2-NH)-Ala-pNA

Refernces

• 1、 Periyalagan, Alagarsamy,Kim, Yong-Tae,Hong, In Seok. "Synthesis and Characterization of Optically Pure Gamma-PNA Backbones by SIBX-Mediated Reductive Amination". . p. 1304 - 1309. Retrieved 2021/08/09.
• 2、 García-Urricelqui, Ane,de Cózar, Abel,Mielgo, Antonia,Palomo, Claudio. "Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases". supporting information. p. 2483 - 2492. Retrieved 2020/12/25.