(4S,5R)-3-Benzoyl-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

Solution of 2-CHLOR-4, 6-dimethoxy-1, 3, 5-triazine (0.175 g, 1 mmole) in 5 ML THF was mixed with N-METHYLMORPHOLINE (D ML, 1 mmole) for 30 minutes at temperature of 0- 5C, to form respective quaternary TRIAZINILAMMONIUM salt. Then, phenyl isoserine of the formula 4b, where R3= R4=CH3 (0 325 g, 1 MMOL) was added and mixed for 12 hours, first at temperature of 0-5C, next at room temperature. N-METHYLMORPHOLINE was filtered off and solvent was removed from the filtrate. It gave respective triazine ester of the formula 6b, where R3=R4=CH3, R5=R6=OCH3, with the quantitative yield. TLC : ELUENT CHCI3, RF=0. 50 'H-NMR (COCI3) : 5= 1.76 (s, 3H); 1.79 (s, 3H); 3.76 (s, 6H); 5.20 (d, J= 7.5 Hz, 1H) ; 5.59, (d, J= 7.5 Hz, 1 H) ; 7.43-7. 56 (m, 8H) ; 7.70-7. 43 (m, 2H) [ppm]. IR (KBr): 1790 [CM~1] The triazine ester was coupled with protected Baccatin (it of generalized formula 3, where R2=Si (C2HS) 3, in the presence of magnesium bromide and diazobicycloundekane. It gave 0.945 g of the final product (93.8%) with the melting temperature of 171-173C. TLC: eluent (acetone: benzene 1: 4), RF=0. 85 1H-NMR (CDCI3) : 6=0. 55 (q, J=8. 5 Hz, 6H); 0.94 (t, J=8.5 Hz, 9H); 1.17 (s, 3H) ; 1.22 (s, 3H); 1.67 (s, 3H); 1.77 (s, 1H) ; 1.83-1. 85 (m, 1H) ; 1.87 (s, 3H); 1.94 (s, 3H); 2.02 (s, 3H); 2.07 (s, 3H); 2.02-2. 18 (m, 2H); 2.19 (s, 3H); 2.07-2. 20 (m, 2H); 2.48-2. 50 (m, 2H); 3.77 (d, J=7.5 Hz, 1H) ; 4.07 (d, J=8.5 Hz, 1H) ; 4.25 (d, J=8.5 Hz, 1H) ; 4.42-4. 46 (m, 1H) ; 4.58 (d, J=7.5 HZ, 1H) ; 4.88-4. 93 (m, 1H) ; 5.28 (d, J=6. 5 Hz, 1H) ; 5.68 (d, J=7.5 Hz, 1H) ; 6.21- 6.25 (m, 1H) ; 6.49 (s, 1H) ; 6.91-6. 96 (m, 1H) ; 7.07-7. 22 (m, 8H); 7.44-7. 48 (m, 2H) ; 7.61- 7.65 (m, 1 H) ; 8.02 (d, J=7.5 Hz, 2H) [ppm] The product of condensation was treated with formic acid in THF, and the final product was CHROMATOGRAPHICALLY PURIFIED on silica gel with the system of hexane: ethyl acetate 2: 1. It gave 0.621 G (yield 76%) of a product spectroscopically and CHROMATOGRAPHICALLY identical to Paclitaxel.Solution OF 2-CHLOR-4, 6-DIPHENOXY-1, 3, 5-triazine (CDPHT) (0. 3 g, 1 mmole) in 5 mi THF was mixed with N-methylmorpholine (0.11 ml, 1 mmole) for 30 minutes at temperature of 0-5C to obtain N- (4, 6- DIPHENOXY-1, 3, 5-triazine-2-yl)-N- methylmorpholine chloride. Then, phenyl isoserine derivative with the formula 4b, where R3= R4=CH3 (0.325 g, 1 mmol) was added and mixed for 12 hours. After N-METHYLMORPHOLINE HYDOCHLORIDE was filtered off, and solvent was evaporated it gave respective triazine ester of the formula 6b, where R3= R4=CH3, and R5=R6= OCEHG, with the quantitative yield. TLC: eluent CHCI3, RR0. 65 1H-NMR (CDCI3) : 6=1. 76 (s, 3H); 1.79 (s, 3H) ; 5.19 (d, J=8.0 Hz, 1H); 5.27 (d, J= 8. 0 Hz, 1H) ; 7.19-7. 22 (m, 2H); 7.40-7. 74 (m, 18 H) ppm] JR (KBr): 1780 [CM~1] The triazine ester, in the presence of magnesium bromide and PYROLIDINPYRIDINE, was coupled with protected Baccatin III of the generalized formula 3, where R2=Si (C2H5) 3. The product was chromatographically and SPECTRALLY identical to that described in the 11. Example.

Molecular Weight:325.4
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:325.13140809
Monoisotopic Mass:325.13140809
Topological Polar Surface Area:66.8
Heavy Atom Count:24
Complexity:478
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes