204320-51-4

Basic information

• Product Name: FMOC-COP
• Synonyms: FMOC-COP;FMOC-COP-OH;FMOC-(R,S)-2-CARBOXYMORPHOLINE;(R,S)-FMOC-2-CARBOXYMORPHOLINE;(R/S)-FMOC-3-CARBOXYMORPHOLINE;RARECHEM EM WB 0088;4-Fmoc-3-morpholinecarboxylicacid;4-[(9H-Fluoren-9-ylmethoxy)carbonyl]morpholine-2-carboxylic acid
• CAS NO: 204320-51-4
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.37
• Product Categories: pharmacetical
• Mol File: 204320-51-4.mol

Chemical Properties

• Boiling Point: 579.8°C at 760 mmHg
• Flash Point: 304.4°C
• Appearance: /
• Density: 1.344g/cm³
• Vapor Pressure: 2.77E-14mmHg at 25°C
• Refractive Index: 1.621
• PKA: 3.47±0.20(Predicted)
• CAS DataBase Reference: FMOC-COP(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-COP(204320-51-4)
• EPA Substance Registry System: FMOC-COP(204320-51-4)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• HazardClass: IRRITANT
• Hazardous Substances Data: 204320-51-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H19NO5/c22-19(23)18-12-25-10-9-21(18)20(24)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,17-18H,9-12H2,(H,22,23)

Upstream product

• 942153-02-8 (3R)-morpholine-3,4-dicarboxylic acid 4-(9H-fluoren-9-ylmethyl) ester 3-methyl ester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 106825-81-4 (3R)-morpholine-3-carboxylic acid 
• 942153-00-6 (2R)-2-[(2,2-dimethoxyethylamino)(9H-fluoren-9-ylmethoxycarbonyl)amino]-3-hydroxypropionic acid methyl ester 
• 942153-01-7 (3R)-2,3-dihydro[1,4]oxazine-3,4-dicarboxylic acid 4-(9H-fluoren-9-ylmethyl) ester 3-methyl ester 
• 783350-37-8 (S)-4-[(tert-butoxy)carbonyl]morpholine-3-carboxylic acid 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 106825-79-0 (S)-morpholine-3-carboxylic acid 
• 1187929-04-9 (3S)-morpholine-3-carboxylic acid hydrochloride salt 
• 942152-96-7 (2S)-2-[(2,2-dimethoxyethylamino)(9H-fluoren-9-ylmethoxycarbonyl)amino]-3-hydroxypropionic acid methyl ester 
• 942152-97-8 (3S)-2,3-dihydro[1,4]oxazine-3,4-dicarboxylic acid 4-(9H-fluoren-9-ylmethyl) ester 3-methyl ester 

Relevant articles and documents

Convenient route to enantiopure Fmoc-protected morpholine-3-carboxylic acid

(Chemical Equation Presented) Enantiopure Fmoc-protected morpholine-3-carboxylic acid was synthesized from dimethoxyacetaldehyde and serine methyl ester through a short and practical synthetic route. The preparation consisted of a five-step process based on reductive amination, intramolecular acetalization, and concomitant elimination of the anomeric methoxy substituent, followed by hydrogenation of the double bond and final acidic ester hydrolysis. The optical purity of both enantiomers of the title amino acid was demonstrated by HPLC analysis of the corresponding amide derivatives obtained from coupling with chiral (S)-(-)-1-phenylethylamine. Moreover, the synthesis of a model tripeptide showed full compatibility of the title Fmoc-amino acid with solid-phase peptide synthesis, thus allowing the application of Fmoc-morpholine-3-carboxylic acid in peptidomimetic chemistry on the solid phase.

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Chemical scale studies of the Phe-Pro conserved motif in the cys loop of cys loop receptors

The functions of two conserved residues, Phe135 and Pro 136, located at the apex of the Cys loop of the nicotinic acetylcholine receptor are investigated. Both residues were substituted with natural and unnatural amino acids, focusing on the role of aromaticity at Phe135, backbone conformation at Pro136, side chain polarity and volume, and the specific interaction between the aromatic side chain and the proline. NMR spectroscopy studies of model peptides containing proline and unnatural proline analogues following a Phe show a consistent increase in the population of the cis conformer relative to peptides lacking the Phe. In the receptor, a strong interaction between the Phe and Pro residues is evident, as is a strong preference for aromaticity and hydrophobicity at the Phe site. A similar influence of hydrophobicity is observed at the proline site. In addition, across a simple homologous series of proline analogues, the results reveal a correlation between receptor function and cis bias at the proline backbone. This could suggest a significant role for the cis proline conformer at this site in receptor function.

An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulfonium salts

(Chemical Equation Presented) Heterocycling: Diphenyl vinyl sulfonium salt 1 acts first as an electrophile, then a base, and then again as an electrophile in this operationally simple, high yielding, one-pot synthesis of pharmacologically important morpholines, thiomorpholines, and piperazines. Compound 1 is an excellent synthon for the 1,2-ethane dication.