(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid Chemical Properties

Melting point:

134-138℃

Boiling point:

573.8±50.0 °C(Predicted)

Density 

1.238

storage temp. 

2-8°C

pka

2.99±0.60(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C22H25NO6/c1-22(2,3)29-21(26)23-17(14-8-6-5-7-9-14)18(20(24)25)28-19(23)15-10-12-16(27-4)13-11-15/h5-13,17-19H,1-4H3,(H,24,25)/t17-,18+,19?/m0/s1

InChIKey

MSVWUXLRSKRKFZ-PAMZHZACSA-N

SMILES

O1[C@@H](C(O)=O)[C@H](C2=CC=CC=C2)N(C(OC(C)(C)C)=O)C1C1=CC=C(OC)C=C1

Safety Information

Safety Statements 

24/25

HS Code 

29349990

(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid Usage And Synthesis

Chemical Properties

White solid

Uses

(4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidine carboxylic acid is an intermediate/impurity for docetaxel hydrate (D494420). It can also be used to synthesize quinoline-docetaxel analogues which exhibit anticancer activity.

Synthesis

The (4S,5R)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid precursor obtained in the previous step (4.83 g, 9.88 mmol) was dissolved in 10 mL of methanol and 1.0 g of palladium hydroxide was added as a catalyst. Hydrogen was introduced into the reaction system at room temperature (pressure maintained at 20 psi) and the reaction was carried out for 1 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure and purified by column chromatography (eluent ratio of petroleum ether/ethyl acetate = 5:1) to afford (4S,5R)-3-(tert-butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-oxazolidine-5-carboxylic acid as a white solid (2.68 g, 67.9% yield).

References

[1] Patent: US2016/340365, 2016, A1. Location in patent: Paragraph 0140; 0141
[2] Patent: US2016/297784, 2016, A1. Location in patent: Paragraph 0149; 0164; 0165
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 194 - 203

(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid (196404-55-4)Related Product Information

• Docetaxel Metabolite M4
• 7-{[(2,2,2,-TRICHLOROETHYL)OXY]CARBONYL} BACCATIN III
• 2',3'-O,N-[(S)-(p-Methoxybenzylidene)]-7-O-(triethylsilyl)paclitaxel
• Deacetyltaxol
• 7-O-(TRIETHYLSILYL) BACCATIN III
• 7,10-Dimethoxy-10-DAB III
• (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylic acid
• Cabazitaxel
• Docetaxel intermediate
• 10-Deacetylbaccatin III
• Paclitaxel
• Cabazitaxel N-1
• (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid
• Docetaxel
• 10-Oxo Docetaxel
• 2-Debenzoyl-2-pentenoyl Docetaxel
• (2S,4S,5R)-3-Boc-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic Acid
• Docetaxel Impurity 5