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Tert-butyl [(1S)-1-benzyl-2-oxo-2-pyrrolidin-1-ylethyl]carbamate is a carbamate derivative with the molecular formula C21H30N2O3. It features a tert-butyl group, a pyrrolidin-1-yl moiety, and benzyl and oxo substituents. This chemical compound is known for its role in organic synthesis and as a reagent in various chemical reactions.

125139-05-1

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  • Carbamic acid, [(1S)-2-oxo-1-(phenylmethyl)-2-(1-pyrrolidinyl)ethyl]-, 1,1-dimethylethyl ester

    Cas No: 125139-05-1

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  • Carbamic acid, [(1S)-2-oxo-1-(phenylmethyl)-2-(1-pyrrolidinyl)ethyl]-, 1,1-dimethylethyl ester

    Cas No: 125139-05-1

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125139-05-1 Usage

Uses

Used in Organic Synthesis:
Tert-butyl [(1S)-1-benzyl-2-oxo-2-pyrrolidin-1-ylethyl]carbamate is used as a reagent in organic synthesis for the preparation of various chemical compounds. Its unique structure and functional groups enable it to participate in a range of chemical reactions, facilitating the synthesis of target molecules.
Used in Pharmaceutical Drug Development:
Tert-butyl [(1S)-1-benzyl-2-oxo-2-pyrrolidin-1-ylethyl]carbamate may possess pharmacological properties, making it a valuable component in the development of pharmaceutical drugs. Its potential therapeutic effects can be harnessed to create new medications for various medical conditions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, tert-butyl [(1S)-1-benzyl-2-oxo-2-pyrrolidin-1-ylethyl]carbamate is employed for the design and synthesis of novel therapeutic agents. Its structural features and reactivity can be utilized to create innovative compounds with potential applications in treating diseases and improving human health.
Overall, tert-butyl [(1S)-1-benzyl-2-oxo-2-pyrrolidin-1-ylethyl]carbamate is a versatile chemical compound with applications in organic synthesis, pharmaceutical drug development, and medicinal chemistry. Its unique structure and properties make it a valuable asset in the creation of new chemical entities and therapeutic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 125139-05-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,5,1,3 and 9 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 125139-05:
(8*1)+(7*2)+(6*5)+(5*1)+(4*3)+(3*9)+(2*0)+(1*5)=101
101 % 10 = 1
So 125139-05-1 is a valid CAS Registry Number.

125139-05-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl N-[(2S)-1-oxo-3-phenyl-1-pyrrolidin-1-ylpropan-2-yl]carbamate

1.2 Other means of identification

Product number -
Other names I14-8851

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:125139-05-1 SDS

125139-05-1Relevant articles and documents

An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry

Ibrahim, Tarek S.,Seliem, Israa A.,Panda, Siva S.,Al-Mahmoudy, Amany M.M.,Abdel-Samii, Zakaria K.M.,Alhakamy, Nabil A.,Asfour, Hani Z.,Elagawany, Mohamed

, (2020/06/17)

A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

Cytotoxic activity of synthetic chiral amino acid derivatives

de Castro, Pedro P.,Siqueira, Raoni P.,Conforte, Luiza,Franco, Chris H.J.,Bressan, Gustavo C.,Amarante, Giovanni W.

, p. 193 - 200 (2019/12/28)

Cancer is a chronic degenerative disease considered one of the most important causes of death worldwide. In this context, a series of dual-protected amino acid derivatives was synthesized and evaluated as potential novel anticancer agents. The 40 derivatives were prepared in up to three reaction steps. The cytotoxic activities were screened in vitro against a panel of tumor and non-tumor cells using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among the synthesized derivatives, three of them showed promising activity against cancer cells with half-maximal inhibitory concentration (IC50) ranging between 1.7-6.1 μM. The most promising derivative, bearing both a lipophilic N-alkyl diamine moiety and a protected amino acid scaffold showed a selectivity index of 3.4 towards tumor cells. The N-alkyl diamine moiety seems to play a crucial role in the enhancement of the anticancer activity. On the other hand, the incorporation of an amino acid scaffold resulted in increase in the selectivity towards cancer cell lines.

Dual-protected amino acid derivatives as new antitubercular agents

de Castro, Pedro P.,Campos, Débora L.,Pavan, Fernando R.,Amarante, Giovanni W.

, p. 1576 - 1580 (2018/06/06)

Tuberculosis is an infectious disease with high incidence and growing drug-resistant rates. In an attempt to develop new antitubercular agents, 35 compounds were synthesized, most of them bearing a carbamate and enantiopure amino acid moiety. These compounds had their activity evaluated toward a Mycobacterium tuberculosis strain (ATCC 27294) and cytotoxicity against fibroblast MRC-5 cells (ATCC CCL-171). Three of the prepared derivatives presented a good antimicrobial inhibition and two of them a moderate cytotoxicity. The lipophilicity seems to play a vital role in the cell growth activity, with best results for the derivatives with a higher logP.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

Bai, Jianfei,Zambron, Bartosz K.,Vogel, Pierre

supporting information, p. 604 - 607 (2014/04/03)

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3

Lanigan, Rachel M.,Starkov, Pavel,Sheppard, Tom D.

, p. 4512 - 4523 (2013/06/05)

B(OCH2CF3)3, prepared from readily available B2O3 and 2,2,2-trifluoroethanol, is as an effective reagent for the direct amidation of a variety of carboxylic acids with a broad range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good to excellent yield, via transamidation of dimethylformamide.

Chiral primary amine catalyzed asymmetric direct cross-aldol reaction of acetaldehyde

Hu, Shenshen,Zhang, Long,Li, Jiuyuan,Luo, Sanzhong,Cheng, Jin-Pei

experimental part, p. 3347 - 3352 (2011/08/03)

The first primary aminocatalytic direct cross-aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L-tert-leucine derivative 1c in conjunction with (H4SiW 12O40)0.25 was identified as the optimal catalyst; good catalytic activity (up to 99% yield in 4 h), and high enantioselectivities (up to 92% ee) were achieved for a range of donors, including aromatic aldehydes and isatin derivatives. Aqueous acetaldehyde solution and paraldehyde can be conveniently applied in this system.

Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases

Saito, Yukako,Ouchi, Hidekazu,Takahata, Hiroki

experimental part, p. 11129 - 11135 (2009/04/11)

Formation of carboxamides of a variety of carboxylic acids with the coupling reagent BBDI is described. This procedure permits a one pot and simple operation without the need of any bases and no base was?required for even use of amine hydrochlorides. In addition, an approach to BBDI-catalyzed carboxamidation is examined.

A new chiral synthesis of a bicyclic enedione containing a seven-membered ring mediated by a combination of chiral amine and Bronsted acid

Nagamine, Takashi,Inomata, Kohei,Endo, Yasuyuki

experimental part, p. 1191 - 1204 (2009/06/28)

Several chiral amines bearing a heterocyclic moiety such as pyrrolidine, piperazine or tetrazole were prepared from l-phenylalanine. The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by a combination of the synthetic chiral a

Efficient transamidation of primary carboxamides by in situ activation with N,N-dialkylformamide dimethyl acetals

Dineen, Thomas A.,Zajac, Matthew A.,Myers, Andrew G.

, p. 16406 - 16409 (2007/10/03)

Two protocols for the transamidation of primary amides with primary and secondary amines, forming secondary and tertiary amides, respectively, are described. Both processes employ N,N-dialkylformamide dimethyl acetals for primary amide activation, producing N-acyl-N,N-dialkylformamidines as intermediates, as widely documented in the literature. Although the latter intermediates react irreversibly with amines by amidinyl transfer, we show that in the presence of certain Lewis acid additives efficient acyl transfer occurs, providing new and useful methods for amide exchange. In one protocol for transamidation, the N-acyl-N,N-dialkylformamidine intermediates are purified by flash-column chromatography and the purified intermediates are then treated with an amine (typically, 2.5 equiv) in the presence of scandium triflate (10 mol %) in ether to form in high yields the products of transamidation. In a second procedure, N-acyl-N,N-dialkylformamidines are generated in situ and, without isolation, are subjected to transamidation in the presence of zirconium chloride (0.5 equiv) and an amine (typically 2 equiv). A variety of different primary amides and amines are found to undergo efficient transamidation using the methods described.

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