(S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine

Base Information

• Chemical Name: (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine
• CAS No.: 153782-96-8
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol file: 153782-96-8.mol

Synonyms:(S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine

Chemical Property of (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine

There total 11 articles about (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine 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: 99.0%

(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-phenyl-O-(4-methylphenylsulfonyl)propan-1-ol (141403-49-8,72196-67-9) → (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine (153782-96-8)

Guidance literature:

With potassium diphenylphosphine; In tetrahydrofuran; Ambient temperature;

DOI:10.1002/hlca.19980810506

Reference yield: 86.0%

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine (153782-96-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2h; 0 deg C -> room temperature;

DOI:10.1016/0040-4039(93)88092-W

Reference yield:

L-Phenylalaninol (3182-95-4) → (S)-N-t-butoxycarbonyl-2-phenylmethyl aziridine (153782-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 3 h / 20 °C

2: KOH; p-TsCl / tetrahydrofuran / 4 h / Heating

With potassium hydroxide; p-toluenesulfonyl chloride; In tetrahydrofuran; acetonitrile;

DOI:10.1055/s-2005-871546

upstream raw materials:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-phenyl-O-(4-methylphenylsulfonyl)propan-1-ol

(2S)-2-benzylazacyclopropane

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (S)-(1-phenyl-3-(phenylselanyl)propan-2-yl)carbamate

(2S)-1-(benzylselanyl)-3-phenylpropan-2-amine

(S)-4-Benzyl-2-oxazolidinone

(S)-tert-butyl (1-mercapto-3-phenylpropan-2-yl)carbamate

Refernces

• 1、 Cheviet, Thomas,Peyrottes, Suzanne. "Synthesis of Aminomethylene- gem-bisphosphonates Containing an Aziridine Motif: Studies of the Reaction Scope and Insight into the Mechanism". . p. 3107 - 3119. Retrieved 2021/02/05.
• 2、 Flentge, Charles A.,Randolph, John T.,Huang, Peggy P.,Klein, Larry L.,Marsh, Kennan C.,Harlan, John E.,Kempf, Dale J.. "Synthesis and evaluation of inhibitors of cytochrome P450 3A (CYP3A) for pharmacokinetic enhancement of drugs". supporting information; experimental part. p. 5444 - 5448. Retrieved 2010/05/02.