2019-72-9

Basic information

• Product Name: N-methylamide of D-(-)-mandelic acid
• CAS NO: 2019-72-9
• Molecular Weight: 165.192
• Mol File: 2019-72-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: N-methylamide of D-(-)-mandelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylamide of D-(-)-mandelic acid(2019-72-9)
• EPA Substance Registry System: N-methylamide of D-(-)-mandelic acid(2019-72-9)

Safety Data

• Hazardous Substances Data: 2019-72-9(Hazardous Substances Data)

Upstream product

• 623-59-6 N-acetyl-N'-methylurea 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 74-89-5 methylamine 
• 121726-59-8 N-phenylacetyl-O-acetyl-N-methylhydroxylamine 
• 83490-71-5 N?methyl?2?oxo?2?phenylacetamide 
• 6830-82-6 N-methylphenylacetamide 
• 103-80-0 phenylacetyl chloride 
• 100-52-7 benzaldehyde 
• 20342-65-8 2-hydroxypropanedinitrile 
• 141694-25-9 N-methoxy-N-methyl-α-oxo-benzeneacetamide 
• 72229-75-5 N-Hydroxy-N-methyl-2-phenylacetamide 
• 67-56-1 methanol 
• 671777-78-9 N-methyl-2-oxo-2-phenyl-N-trimethylsilanylmethyl-acetamide 

Downstream Products

• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 151414-64-1 2-trimethylsilyloxy-2-phenylacetic acid N-methylamide 
• 84694-26-8 2-phenyl>-3-methyl-5(R)-phenyloxazolidine 
• 495-42-1 (-)-Halostachine 
• 89843-35-6 (R)-N-methyl mandelamide 
• 65645-88-7 (S)-α-hydroxy-N-methyl-2-phenylacetamide 
• 83490-71-5 N?methyl?2?oxo?2?phenylacetamide 
• 88953-55-3 α-phenyl-β-(N-methylformamido)ethanol 
• 88953-56-4 3-methyl-5-phenyloxazolidine 
• 303030-24-2 2,3-Dimethyl-5-phenyl-1,3-oxazolidin-4-on 
• 151414-66-3 N-methyl-N-amide of 2-trimethylsilyloxy-2-phenylacetic acid 
• 151414-68-5 2,2,4-trimethyl-6-phenyl-1-oxa-4-aza-2-silacyclohexan-5-one 
• 89881-08-3 (N-methylcarbamoyl)(phenyl)methyl acetate 
• 157737-59-2 (+/-)-O,N-Bis(trimethylsilyl)mandelsaeure-methylamid 

Relevant articles and documents

155. N-Methyl-C-(trichlortitanio)formimidoylchlorid. Ein effizientes Reagenz zur Homologisierung von Aldehyden und Ketonen zu α-Hydroxy-carbonsaeureamiden

The known title compound 6 formed by addition of titanium tetrachloride to methyl isocyanide in methylene chloride adds to the carbonyl group of aldehydes and ketones.The adducts 7 are hydrolized to N-methyl-α-hydroxycarboxamides 8 which are (from ketones) or are not branched (from aldehydes) in the α-position.The yields in this new modification of the Passerini reaction are near 90percent, also with readily enolized ketones such as acetone and acetophenone.In contrast to the previously used organotitanium reagents of the type RTiX3, the preparation of the reagent 6 does not require any Li-, Mg- or Zn-derivative as a precursor.

Selective α-Oxyamination and Hydroxylation of Aliphatic Amides

Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.

Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides

Asymmetric hydrogenation of α-keto Weinreb amides has been realized with [Ru((S)-Sunphos)(benzene)Cl]Cl as the catalyst and CeCl3· 7H2O as the additive. A series of enantiopure α-hydroxy Weinreb amides (up to 97% ee) have been obtained. Catalytic amount of CeCl 3·7H2O is essential for the high reactivity and enantioselectivity and the ratio of CeCl3·7H2O to [Ru((S)-Sunphos)(benzene)Cl]Cl plays an important role in the hydrogenation reaction.