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H-D-PHG-OME HCL

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CAS:19883-41-1
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CAS:19883-41-1
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H-D-PHG-OME HCL Basic information
Product Name:H-D-PHG-OME HCL
Synonyms:Methyl α-aMinophenylacetate HCl;(R)-Methyl 2-aMino-2-phenylacetate hydrochloride;(2-keto-2-methoxy-1-phenyl-ethyl)ammonium chloride;(2-methoxy-2-oxo-1-phenylethyl)ammonium chloride;(2-methoxy-2-oxo-1-phenyl-ethyl)ammonium chloride;(2-methoxy-2-oxo-1-phenylethyl)azanium chloride;(2-methoxy-2-oxo-1-phenyl-ethyl)azanium chloride;methyl amino(phenyl)acetate hydrochloride
CAS:19883-41-1
MF:C9H12ClNO2
MW:201.65
EINECS:243-399-9
Product Categories:Phenylglycine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives;Phenylglycine [Phg];Amino Acids
Mol File:19883-41-1.mol
H-D-PHG-OME HCL Structure
H-D-PHG-OME HCL Chemical Properties
Melting point 189-191 °C(lit.)
alpha -118o (C=1 IN H2O)
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form powder to crystal
color White to Almost white
Optical Rotation[α]20/D 118°, c = 1 in H2O
BRN 3915654
Major Applicationpeptide synthesis
InChIInChI=1/C9H11NO2.ClH/c1-12-9(11)8(10)7-5-3-2-4-6-7;/h2-6,8H,10H2,1H3;1H/t8-;/s3
InChIKeyDTHMTBUWTGVEFG-DDWIOCJRSA-N
SMILESC(OC)(=O)[C@H](C1=CC=CC=C1)N.[H]Cl |&1:4,r|
CAS DataBase Reference19883-41-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36
Safety Statements 26-36/37
WGK Germany 3
HS Code 29224999
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
H-D-PHG-OME HCL Usage And Synthesis
Chemical PropertiesWhite solid
Uses(R)-(-)-2-Phenylglycine Methyl Ester Hydrochloride is an intermediate in the synthesis of Cephradine, a cephalosporin antibiotic. It functions as an acyl donor in the enzymatic synthetic process for cephradine synthesis.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
Methanol

67-56-1

D-2-Phenylglycine

875-74-1

H-D-PHG-OME HCL

19883-41-1

Methylation reaction of L-phenylglycine. L-phenylglycine (1 g, 6.05 mmol, 1.0 eq.) was suspended in methanol (25 mL) and cooled to 0°C. Thionyl chloride (475 μL, 6.66 mmol, 1.5 eq.) was slowly added. after 10 min, the reaction mixture was heated to 75 °C and refluxed for 2 h. The reaction was completed by TLC. After completion of the reaction (monitored by TLC), the solvent was removed under vacuum to give a white solid, L-phenylglycine methyl ester hydrochloride (1.23 g, quantitative yield).

References[1] Tetrahedron, 1999, vol. 55, # 11, p. 3337 - 3354
[2] European Journal of Organic Chemistry, 2009, # 30, p. 5185 - 5191
[3] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660
[4] Tetrahedron, 2009, vol. 65, # 6, p. 1200 - 1206
[5] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1992, # 8, p. 1279 - 1285
H-D-PHG-OME HCL Preparation Products And Raw materials
Raw materialsMethanol-->D-2-Phenylglycine
Preparation Products1,4-Diazabicyclo[2.2.2]octane, 2-phenyl-, (2R)-
Tag:H-D-PHG-OME HCL(19883-41-1) Related Product Information
Glycine ethyl ester hydrochloride Sodium iodide Glycine methyl ester hydrochloride ETHYL (R)-(-)-MANDELATE Di-tert-butyl peroxide (R)-4-CHLORO PHENYLGLYCINE H-D-PHG-OTBU HCL D(-)-Phenylglycinamide H-D-Phg-Gly-OH METHYL (2R)-2-AMINO-3-(2,6-DIFLUOROPYRIDIN-3-YL)PROPANOATE METHYL (2R)-2-AMINO-3-(2-CHLORO(4-PYRIDYL))PROPANOATE METHYL (2R)-2-AMINO-3-(2,6-DICHLORO(3-PYRIDYL))PROPANOATE METHYL (2R)-2-AMINO-3-(2,6-DIMETHYL(3-PYRIDYL))PROPANOATE methyl (R)-aminophenylacetate methyl (2R)-2-amino-3-(2-fluorophenyl)propanoate hydrochloride METHYL (2R)-2-AMINO-3-(2-AMINO-4-FLUOROPHENYL)PROPANOATE (Z)-Cefdinir Cefdinir Impurity E