1-(1,1-Dimethylethyl) 2-methyl (2S,4R)-4-[[(4-methylphenyl)sulfonyl]oxy]-1,2-pyrrolidinedicarboxylate

N-Boc-trans-4-tosyloxy-L-proline methyl ester is Colourless crystals

1 -ter-Butyl-2-methyl-(25, 4^To a stirred solution of compound 2 (123.0 g, 502 mmol) in DCM (1 L) , EtTo a solution of trans-N-Boc-4-hydroxy-L-proline methyl ester (45 g, 0.183 mol) in pyridine (140 ml) and dry DCM (140 ml) at 0° C. was added dropwise 4-methyl-benzenesulfonyl chloride (41.9 g, 0.22 mol). Compound 6 (4R)-Hydroxy-N-Boc-L-proline methyl ester (25 g, 87 mmol, 1 eq)Soluble150ml of dichloromethane, Pyridine (15.4 ml, 191 mmol, 2.2 eq) was added.The ice bath is cooled to 0 to 5 °C.At this temperature, p-toluenesulfonyl chloride (23.3 g, 104.4 mmol, 1.2 eq) was added portionwise, and the reaction was stirred for 3 h.The TLC detects that the starting material is completely reactive.50 ml of water was added to the reaction solution.Stir for 15min, Let stand layering, The aqueous layer was extracted with 50 ml of dichloromethane.Combine methylene chloride, Wash with salt water, Dry over anhydrous sodium sulfate, concentrate.Residue column chromatography (PE: EA = 8:1) yielded about 33.8 g of colorless oil (yield: 88.0percent).To a solution of 5 (11 g, 45 mmol) in dichloromethane (35 ml) at 0 °C was added toluenesulfonyl chloride (10.27 g, 53.9 mmol) and pyridine (35 ml). After stirring under reflux for 24 h, the reaction mixture was concentrated in vacuo and redissolved in dichloromethane. It was then washed with a saturated aqueous solution of copper sulfate and brine. The organic fraction was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide the product as light yellow liquid (12.6 g, 70percent). ‘H NMR (300 MHz, CDC13) 7.79 (d, J= 8.29 Hz, 2H), 7.36 (d, J 8.10 Hz, 2H), 4.99 - 5.09 (m, 1H), 4.32 -4.43 (m, 1H), 3.72 (s, 3H), 3.57 - 3.65 (m, 2H), 2.46 (s, 4H), 2.09 - 2.22 (m, J= 8.70 Hz, 1H), 1.36 - 1.44 (m, 9H). MS (ESI) [M+H] 400.3, [M+Naj 422.3.(a)

4-Hydroxy-L-proline (H952376) derivative. Used in the preparation of bicycloazahydantoins, as androgen receptor antagonists

Molecular Weight:399.5
XLogP3:2.6
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:7
Exact Mass:399.13517331
Monoisotopic Mass:399.13517331
Topological Polar Surface Area:108
Heavy Atom Count:27
Complexity:642
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes