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((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0℃; | 96% |
(R)-glycidyl butyrate
benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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% |
carbon dioxide
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
With dmap; C20H14AlNO3 In dichloromethane at 25℃; under 760.051 Torr; for 60h; Sealed tube; stereoselective reaction; | 85% |
N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline
(R)-glycidyl butyrate
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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% |
N-[4(R)-(2,2-dimethyl-1,3-dioxolane-4-yl)methyl]-3-fluoro-4-morpholinylaniline
bis(trichloromethyl) carbonate
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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% |
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0℃; Yield given; |
(R)-glycidyl butyrate
3-fluoro-4-(morpholinyl)aniline
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
Multistep reaction; |
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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 |
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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 |
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol
Conditions | Yield |
---|---|
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 |
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