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4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)

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4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Basic information
Product Name:4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)
Synonyms:4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI);(R)-2-Oxo-4-oxazolidinecarboxylic acid methyl ester;(R)-Methyl 2-oxooxazolidine-4-carboxylate;4-Oxazolidinecarboxylic acid, 2-oxo-, Methyl ester, (R)-;(4R)-(9CI);R-2-Oxo-4-oxazolidinecarboxylic acid;4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-;methyl (R)-2-oxooxazolidine-4-carboxylate
CAS:144542-43-8
MF:C5H7NO4
MW:145.11
EINECS:
Product Categories:CARBOXYLICESTER
Mol File:144542-43-8.mol
4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Structure
4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Chemical Properties
Boiling point 357.8±31.0 °C(Predicted)
density 1.320
storage temp. 2-8°C
pka10.82±0.40(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Usage And Synthesis
Synthesis
Triphosgene

32315-10-9

L-Serine methyl ester hydrochloride

5680-80-8

4-Oxazolidinecarboxylicacid,2-oxo-,methylester(9CI)

96751-61-0

General procedure for the synthesis of methyl 2-oxoxoxazolidine-4-carboxylate from tritiated gas and L-serine methyl ester hydrochloride: a THF solution of tritiated gas (60 mL, 11.4 g, 38.58 mmol, 1.0 eq.) was slowly added to a tetrahydrofuran (THF, 90 mL) suspension of L-serine methyl ester hydrochloride (6 g, 38.58 mmol). The reaction mixture was heated to reflux for 4 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by rapid chromatography on silica gel (eluent ratio: ethyl acetate/hexane = 3:1) to afford the target product methyl 2-oxoxoxazolidine-4-carboxylate (4.38 g, 78% yield) as a white solid.

References[1] Chemistry - A European Journal, 2007, vol. 13, # 1, p. 135 - 149
[2] Recueil des Travaux Chimiques des Pays-Bas, 1995, vol. 114, # 4-5, p. 163 - 170
[3] Tetrahedron Letters, 1995, vol. 36, # 49, p. 8961 - 8964
[4] Journal of the American Chemical Society, 1999, vol. 121, # 33, p. 7509 - 7516
[5] Organic Letters, 2011, vol. 13, # 22, p. 6010 - 6013
4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI) Preparation Products And Raw materials
Raw materialsTriphosgene-->L-Serine methyl ester hydrochloride-->Potassium carbonate
Tag:4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4R)-(9CI)(144542-43-8) Related Product Information
4-Oxazolidinecarboxylicacid,2-oxo-,methylester,(4S)-(9CI) 4-Oxazolidinecarboxylicacid,2-oxo-,methylester(9CI) (S)-4-(Hydroxymethyl)oxazolidin-2-one 2-Oxazolidinone, 4-(hydroxyMethyl)-, (4R)- 2-oxo-1,3-oxazolidine-4-carboxylic acid(SALTDATA: FREE) 4-(Hydroxymethyl)oxazolidin-2-one