82270-62-0

Basic information

• Product Name: (S)-N-benzylmandelamide
• Synonyms: (S)-N-benzylmandelamide
• CAS NO: 82270-62-0
• Molecular Weight: 241.29
• Mol File: 82270-62-0.mol

Chemical Properties

• CAS DataBase Reference: (S)-N-benzylmandelamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-benzylmandelamide(82270-62-0)
• EPA Substance Registry System: (S)-N-benzylmandelamide(82270-62-0)

Safety Data

• Hazardous Substances Data: 82270-62-0(Hazardous Substances Data)

Upstream product

• 28193-70-6 N-benzyl-2-oxo-2-phenylacetamide 
• 21210-43-5 (S)-Methyl mandelate 
• 100-46-9 benzylamine 
• 4358-86-5 (S)-mandelamide 
• 188025-26-5 S(+)-N-benzyl-O-acetyl mandelamide 
• 17199-29-0 (S)-Mandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 20698-91-3 (R)-methyl mandelate 
• 98-86-2 acetophenone 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 611-73-4 Benzoylformic acid 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 
• 622-79-7 benzyl azide 
• 129313-47-9 O^α-(tert-butyldimethylsilyl)-L-mandelic acid 

Downstream Products

• 188025-26-5 S(+)-N-benzyl-O-acetyl mandelamide 
• 492435-16-2 (S)-N-benzyl-O-isobutyroylmandelamide 
• 492435-15-1 (S)-O-benzoyl-N-benzylmandelamide 
• 503185-09-9 (S)-N-benzyl-O-(3-ethoxycarbonylacryloyl)mandelamide 
• 503185-08-8 (S)-N-benzyl-O-cinnamoylmandelamide 
• 503185-06-6 (S)-N-benzyl-O-heptanoylmandelamide 
• 1190381-19-1 (S)-((S)-2-(benzylamino)-2-oxo-1-phenylethyl) 2-methoxy-2-phenylacetate 
• 1245944-85-7 C₃₆H₄₁FN₂O₅ 
• 1245944-75-5 C₄₃H₄₈N₂O₆ 
• 1224387-04-5 (2-benzylamino-2-oxo-(S)-1-phenylethyl) α-bromopropanoate 
• 1224387-10-3 (2-benzylamino-2-oxo-(S)-1-phenylethyl) α-bromophenylacetate 
• 51096-49-2 (S)-(+)-2-(N-Benzylamino)-1-phenylethanol 

Relevant articles and documents

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

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.

Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides

A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.

Biocatalytic aminolysis of ethyl (S)-mandelate by lipase from Candida antarctica

Enzymes play many roles in the advancement of biotechnology, discovery of new therapeutic agents and industrial processes. In this perspective, aminolysis reactions using lipase from Candida antarctica (CAL-B) were performed from ethyl (S)-mandelate and several aliphatic amines (45 °C, hexane, 3–6 h). By means of optimized conditions, amides with excellent isolated yields (60–97%) were synthetized. The biotechnological potential of CAL-B as a promising approach for the synthesis of organic compounds in a more sustainable, rapid, efficient and green chemistry perspective was verified on these results.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

Enantioselective Synthesis of α-Hydroxy Amides and β-Amino Alcohols from α-Keto Amides

Synthesis of enantiomerically enriched α-hydroxy amides and β-amino alcohols has been accomplished by enantioselective reduction of α-keto amides with hydrosilanes. A series of α-keto amides were reduced in the presence of chiral CuII/(S)-DTBM-SEGPHOS catalyst to give the corresponding optically active α-hydroxy amides with excellent enantioselectivities by using (EtO)3SiH as a reducing agent. Furthermore, a one-pot complete reduction of both ketone and amide groups of α-keto amides has been achieved using the same chiral copper catalyst followed by tetra-n-butylammonium fluoride (TBAF) catalyst in presence of (EtO)3SiH to afford the corresponding chiral β-amino alcohol derivatives.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

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.

Biocatalytic reduction of α-keto amides to (R)-α-hydroxy amides using Candida parapsilosis ATCC 7330

Biocatalytic reduction of primary and secondary α-keto amides was accomplished using whole cells of Candida parapsilosis ATCC 7330. The primary (R)-α-hydroxy amides were obtained in good enantiomeric excess (up to 94%) and conversion (88-99%) as compared to the secondary (R)-α-hydroxy amides.

SUBSTITUTED BENZOXAZINONES

The present invention provides substituted oxazinone compounds, such as substituted benzoxazinones, which exhibit potent renin inhibition activities.

SUBSTITUTED (S)-BENZOXAZINONES

The present invention provides enantiomerically pure substituted (S)-benzoxazinone compounds and an extended release formulation of the compounds. The compounds exhibit potent renin inhibition activities and improved bioavailability.

Enantioselective addition of dimethylzinc to α-keto esters

The readily available (+)-N-Benzyl-(S)-mandelamide catalyzes the enantioselective addition of dimethylzinc to α-keto esters to give α-methyl-α-hydroxy esters containing stereogenic quaternary centers with moderate to good yields (56-87%). A good enantioselectivity of the reaction is obtained for aryl and heteroaryl keto esters. For these substrates ee values of 75-90% are obtained. The enantioselectivity is somewhat lower for the substrates bearing an aliphatic chain. Georg Thieme Verlag Stuttgart.