| Identification | Back Directory | [Name]
tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate | [CAS]
112741-49-8 | [Synonyms]
CIVENTICHEM CV-2653
CIVENTICHEM CV-2654
2-Oxo-7a-hydroxy Clopidogrel
(5S,6R)-N-BoC-5,6-diphenyl-2-morpholinone
(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylMorpholine
tert-butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morph
(5R,6S)-(-)-4-Boc-5,6-diphenyl-2-Morpholinone, 98%
(2R,3S)-(-)-2,3-Diphenyl-6-oxomorpholine, N-BOC protected
tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarbox
tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate
(2R,3S)-Tert-butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate
N-BOC(2R, 3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE CARBOXYLATE
ert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE
N-TERT-BUTOXYCARBONYL-(2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE
tert-Butyl (2R,3S)-(-)-2,3-diphenyl-6-oxomorpholine-4-carboxylate
(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylMorpholine
(2R,3S)-tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate
(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester
(2R,3S)-6-Oxo-2,3-diphenyl-morpholine-4-carboxylic acid tert-butyl ester
(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid
1,1-Dimethylethyl Ester
(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid
tert-Butyl Ester,99%e.e.
TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENY L-4-MORPHOLINECARBOXYLATE, 99% (99% EE)
4-Morpholinecarboxylicacid, 6-oxo-2,3-diphenyl-, 1,1-dimethylethyl ester, (2R,3S)-
(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic acid t-butyl ester, 98% (99% ee) | [Molecular Formula]
C21H23NO4 | [MDL Number]
MFCD00074955 | [MOL File]
112741-49-8.mol | [Molecular Weight]
353.41 |
| Chemical Properties | Back Directory | [Melting point ]
206 °C (dec.)(lit.)
| [alpha ]
-87 º (c=5.5 in methylene chloride) | [Boiling point ]
509.6±50.0 °C(Predicted) | [density ]
1.175±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Acetone (Slightly, Heated, Sonicated), Chloroform (Slightly), DMSO (Slightly, Sonicated) | [form ]
Solid | [pka]
-3.28±0.60(Predicted) | [color ]
White to Off-White | [Optical Rotation]
[α]25/D 87°, c = 5.5 in methylene chloride | [InChI]
InChI=1S/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3/t18-,19+/m0/s1 | [InChIKey]
MRUKRSQUUNYOFK-RBUKOAKNSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(=O)O[C@H](C2=CC=CC=C2)[C@@H]1C1=CC=CC=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is Off-white Solid
| [Uses]
Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and colla gen cross-link pyridinolines.
| [Synthesis]
N-Boc-substituted diphenylamino alcohol (1.9 g, 4.2 mmol) was dissolved in toluene (25 mL), p-TsOH (p-TsOH, 70 mg, 0.42 mmol) was added, and the reaction was heated and refluxed at 120 °C overnight. Upon completion of the reaction, it was cooled to room temperature and a solid was precipitated. The solid was collected by filtration, washed with saturated aqueous sodium chloride solution, the organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The yellow solid obtained was recrystallized by anhydrous ethanol (20 mL) to give a white solid. After filtration and drying by rotary evaporation, 1.22 g (2R,3S)-N-tert-butoxycarbonyl-2,3-diphenylmorpholin-6-one was obtained as a white solid in 85% yield. | [References]
[1] Patent: CN104945345, 2017, B. Location in patent: Paragraph 0105; 0107; 0116; 0118
[2] Journal of the American Chemical Society, 1988, vol. 110, # 5, p. 1547 - 1557
[3] Synlett, 2005, # 4, p. 693 - 696
[4] Organic Syntheses, 2003, vol. 80, p. 18 - 30 |
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