| Identification | Back Directory | [Name]
(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid | [CAS]
196404-55-4 | [Synonyms]
Docetaxel intermedaite
Said chain of Docetaxel
side chain of docetaxel
3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-2-(4-Methoxyphenyl)-N-t-boc-4-phenyl-oxazolidine-5-carboxylic acid
5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-2-(4-Methoxy-phenyl)-3-N-Boc-4-phenyl-3,5-oxazolidine carboxylic acid
(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-3-tert-butoxycarbony-2-(4-anisyl)--phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-3-tert-Butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-3-tert-butoxycarbony-2-(4-anisyl)-4-phenyl-5-oxazolidinercarboxylicacid
(4S,5R)-3-tert-Butoxycarbonyl-2-(4-anisyl)-4-phenyl-5-oxazolidinecarboxylic acid
(4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3,5-oxazolidinedicarboxylic acid 3-tert-butyl ester
(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-Methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid
(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-Methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(4R,5R)-3-(2,2-Dimethylpropanoyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid
(4S,5R)-2-(4-methoxyphenyl)-4-phenyl-3,5-Oxazolidinedicarboxylic acid 3-(1,1-dimethylethyl)ester
(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylic acid ISO 9001：2015 REACH
(4S,5R)-3-(tert-Butoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid, 98.5%
3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 3-(1,1-dimethylethyl) ester, (4S,5R)-
(4S,5R)-2-(4-methoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid
Docetaxel Side Chain：(4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3,5-oxazolidinedicarboxylic acid 3-tert-butyl ester | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C22H25NO6 | [MDL Number]
MFCD09837613 | [MOL File]
196404-55-4.mol | [Molecular Weight]
399.44 |
| Chemical Properties | Back Directory | [Melting point ]
134-138℃ | [Boiling point ]
573.8±50.0 °C(Predicted) | [density ]
1.238 | [storage temp. ]
Sealed in dry,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 |
| Hazard Information | Back Directory | [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 |
|
|