Related Experiment Video
Updated: Jun 5, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
Methyl 2-{[(4-hydroxy-phen-yl)(methoxy-carbon-yl)meth-yl]amino-carbon-yl}ethano-ate hemihydrate
Abstract:
In the structure of the title compound, C(13)H(15)NO(6)·0.5H(2)O, the water O atom lies on a twofold rotation axis. The methoxy-carbonyl-methyl and amino groups are essentially coplanar and the methoxy-carbonyl-methyl group makes a dihedral angle of 79.73 (10)° with the mean plane of the hydroxy-phenyl ring. The amino and methoxy-carbonyl-methyl groups are involved in an intra-molecular N-H⋯O hydrogen bond which generates an S(5) ring motif. In the crystal structure, mol-ecules are linked via N-H⋯O and O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into a two-dimensional network parallel to the (01) plane. The crystal structure is further stabilized by C-H⋯π inter-actions.
Related Concept Videos
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Phase II Reactions: Methylation Reactions
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Aldehydes and Ketones with Alcohols: Hemiacetal Formation

