263403-72-1

Basic information

• Product Name: tert-Butyl 2-Boc-aMinobenzylcarbaMate
• Synonyms: tert-Butyl 2-Boc-aMinobenzylcarbaMate;tert-Butyl 2-((tert-butoxycarbonyl)amino)benzylcarbamate
• CAS NO: 263403-72-1
• Molecular Formula: C17H26N2O4
• Molecular Weight: 322.39934
• Mol File: 263403-72-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: tert-Butyl 2-Boc-aMinobenzylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl 2-Boc-aMinobenzylcarbaMate(263403-72-1)
• EPA Substance Registry System: tert-Butyl 2-Boc-aMinobenzylcarbaMate(263403-72-1)

Safety Data

• Hazardous Substances Data: 263403-72-1(Hazardous Substances Data)

Usage

General Description

Tert-butyl 2-Boc-aminobenzylcarbamate is a chemical compound with the formula C17H26N2O4. It is a tert-butyl ester derivative of 2-Boc-aminobenzylcarbamate, which is commonly used as a protecting group in organic synthesis. The tert-butyl group serves as a protecting group for the amine, which can be selectively removed under acidic conditions. tert-Butyl 2-Boc-aMinobenzylcarbaMate is important in the synthesis of various pharmaceuticals and organic compounds, where the protection of the amine group is necessary to control the reactivity and selectivity of chemical reactions.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4403-69-4 2-amino-1-benzylamine 
• 103-82-2 phenylacetic acid 

Relevant articles and documents

Observations concerning the synthesis of heteroatom-containing 9-membered benzo-fused rings by ring-closing metathesis

A set of benzo-fused dienes with a 1,9-relationship and containing a variety of nitrogen and oxygen heteroatoms was readily synthesized. These dienes were then treated with the Grubbs second generation catalyst with the aim of synthesizing the 9-membered benzannelated heterocycles containing two heteroatoms (either O,O, NR,NR or O,NR where R = Ts or Boc). As previously observed in the literature, many of the dienes did not give the expected ring-closed product. However, a number of the desired products did form, namely with the 1,2-dihydrobenzo[c][1,5]oxazonin-7(5H)-one, 5,7-dihydrobenzo[b][1,5]oxazonine-6(2H)-carboxylate and 2,5,6,7-tetrahydrobenzo[b][1,5]oxazonine cores, albeit in poor yields. Rather surprisingly, the N-allyl-N-(2-(N-allyl-4-methylphenylsulfonamido)benzyl)-4-methylbenzenesulfonamide scaffold gave the desired ring-closed 1,6-ditosyl-2,5,6,7-tetrahydro-1H-benzo[b][1,5]diazonine in a high yield. Furthermore, when treated with the catalyst [RuClH(CO)(PPh3)3] the alkene isomerized into conjugation only with the benzylic NTs group and not with the phenyl NTs group to afford the 1,6-ditosyl-2,3,6,7-tetrahydro-1H-benzo[b][1,5]diazonine structure.

Anomals Schmidt reaction products of phenylacetic acid and derivatives

Treatment of carboxylic acids with sodium azide in sulfuric acid normally results in decarboxylation with conversion of the carboxylic acid to an amine (the Schmidt reaction). However, many side reactions have been reported to occur, particulary in the case of α-aryl carboxylic acids, such as sulfonation, direct amination of the phenyl ring, cyclization to a lactam, and elimination of side chains to give aniline. In this study, the reactions of a variety of analogues of phenylacetic acid under given reaction conditions are examined to determine which characteristics are important in the competing side reactions. Some reactions were carried out with TEMPO free radical as a radical scavenger to investigate whether direct amination proceeds by a radical intermediate. Phenylacetic acid is shown to give an ortho-aminated diamine product instead of the para-aminated one expected from direct amination. A mechanism for this side reaction, involving cyclization to a lactam intermediate followed by further cleavage, is proposed; an analogue of the hypothetical intermediate has been isolated for biphenylacetic acids.