4-hydroxy-N,N-diphenyl-(4R)-2-Pentynamide

Preparation of Amide-Method A(R) The following procedures can be operated on either the racemic or the enantiopure starting butyn-2-ol. To a stirred solution of sulfuric acid (cone, 40//L) in THF (24OmL) were sequentially added (R)-3 butyn-2-ol (40g, 0.57 mol) and then hexamethyldisilazane (49.6g, 0.31 mol) at room temperature. The solution was refluxed for 3-4 hours and then slowly cooled to -4OFor deacetylation, TBME was removed and the solution was reconstituted in 100 ml MeOH. The solution was chilled to 5 The identification of the enzyme started from screening 53 commercially available enzymes for the hydrolysis of (R)-(IV). Typically, the reaction mixture in the screen included 20 mg of (R)-(IV) in 0.2 ml toluene, 20 mg of an enzyme, and 0.8 ml of 0.2 M phosphate buffer, pH 7.0. The reaction was agitated at 35 °C for 1.5 h. The conversion was determined by reverse phase HPLC. There were 13 reactions that showed > 30percent conversion (see Table 8). CALB L was picked for further testing. EPO The toluene solution was mixed with 300 ml phosphate buffer (0.1 M) before adding 17 ml CAL B L. (Novozyme, Franklinton, N.C.). The hydrolysis reaction was carried out in a biphasic system. The pH of the aqueous phase was maintained at 7.0 by titration of 2 N NaOH with a pH stat. After 20 h, the conversion reached 51percent, giving (R)-A and (S)-B in 97percent, and 99percent ee, respectively. The reaction mixture was filtered through a celite pad and the aqueous phase was removed.

Molecular Weight:265.31
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:265.110278721
Monoisotopic Mass:265.110278721
Topological Polar Surface Area:40.5
Heavy Atom Count:20
Complexity:362
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes