tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

Product Nametert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
CAS112741-49-8
MFC21H23NO4
MW353.41
EINECS
MOL File112741-49-8.mol

Chemical Properties

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)
pka	-3.28±0.60(Predicted)
form	Solid
color	White to Off-White
optical activity	[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

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	2934999090
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

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.

Uses

(2R,3S)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester is a reactant used in the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G and collagen cross-link pyridinolines.

Synthesis

N-(tert-Butyloxycarbonyl)-N-[(1S,2R)-2-hydroxy-1,2-diphenylethyl]-glycine Ethyl Ester

112741-70-5

tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

112741-49-8

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

Preparation Products And Raw materials

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