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168828-82-8

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Basic Information
CAS No.: 168828-82-8
Name: (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione
Article Data: 26
Molecular Structure:
Molecular Structure of 168828-82-8 ((5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione)
Formula: C14H17FN2O4
Molecular Weight: 296.298
Synonyms: 2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (R)-;S-5-Azidomethyl-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone;(5R)-3-[3-Fluoro-4-(morpholin-4-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one;CHEMBL596913;AC-4277;TL8001308;
EINECS: 688-342-2
Density: 1.362 g/cm3
Melting Point: 110-112 °C
Boiling Point: 494.241 °C at 760 mmHg
Flash Point: 252.708 °C
PSA: 62.24000
LogP: 1.10980
Related products
Synthetic route
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((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃;96%
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(R)-glycidyl butyrate

168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water		85.1%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium; butan-1-ol In tetrahydrofuran; hexane at -15 - 30℃; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -10 - 15℃;
Stage #3: With water In tetrahydrofuran; hexane; ethyl acetate		85%
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.63333h;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃; for 22.1h;		83%
124-38-9

carbon dioxide

(S)-N-(2,3-epoxy-1-propyl)-3-fluoro-4-(4-morpholinyl)aniline

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With dmap; C20H14AlNO3 In dichloromethane at 25℃; under 760.051 Torr; for 60h; Sealed tube; stereoselective reaction;85%
565176-83-2

N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline

60456-26-0

(R)-glycidyl butyrate

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3.5h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water at 20℃; for 0.5h; Product distribution / selectivity;		80%
903593-93-1

N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline

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bis(trichloromethyl) carbonate

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Stage #1: N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline With hydrogenchloride; water In methanol at 20℃; for 8h;
Stage #2: bis(trichloromethyl) carbonate With sodium carbonate at 20℃; for 24h; Further stages.;		56%

(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-carbaldehyde-2-oxazolidinone

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; Yield given;
60456-26-0

(R)-glycidyl butyrate

93246-53-8

3-fluoro-4-(morpholinyl)aniline

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multistep reaction;

3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: aq. NaHCO3 / acetone
2.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
3.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
3.2: NaBH4 / methanol
3.3: 86 percent / CuSO4 / methanol
4.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
912552-55-7

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
1.2: NaBH4 / methanol
1.3: 86 percent / CuSO4 / methanol
2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
912552-54-6

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester

168828-82-8

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
2.2: NaBH4 / methanol
2.3: 86 percent / CuSO4 / methanol
3.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
View Scheme
Raw Materials
93246-53-8
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  • (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidioneCAS NO.: 168828-82-8

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    (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

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  • (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

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    168828-82-8

    (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

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  • (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

  • Casno:

    168828-82-8

    (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione

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  • 2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (5R)-

  • Casno:

    168828-82-8

    2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (5R)-

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Specification

The (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidione with CAS registry number of 168828-82-8 is also known as 2-Oxazolidinone,3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-(hydroxymethyl)-, (5R)-. The IUPAC name is (5R)-3-(3-Fluoro-4-morpholin-4-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one. In addition, the formula is C14H17FN2O4 and the molecular weight is 296.29.

Physical properties about (5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-hydroxymethyl-2-oxazolidion are: (1)ACD/LogP: 0.59; (2)ACD/LogD (pH 7.4): 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 2; (5)ACD/KOC (pH 5.5): 19; (6)ACD/KOC (pH 7.4): 52; (7)#H bond acceptors: 6; (8)#H bond donors: 1; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.572; (11)Molar Refractivity: 71.614 cm3; (12)Molar Volume: 217.595 cm3; (13)Surface Tension: 51.972 dyne/cm; (14)Density: 1.362 g/cm3; (15)Flash Point: 252.708 °C; (16)Enthalpy of Vaporization: 80.203 kJ/mol; (17)Boiling Point: 494.241 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1COCCN1C2=C(C=C(C=C2)N3CC(OC3=O)CO)F
2. Isomeric SMILES: C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3=O)CO)F
3. InChI: InChI=1S/C14H17FN2O4/c15-12-7-10(17-8-11(9-18)21-14(17)19)1-2-13(12)16-3-5-20-6-4-16/h1-2,7,11,18H,3-6,8-9H2/t11-/m1/s1
4. InChIKey: OLDRPBWULXUVTL-LLVKDONJSA-N