3-[(1R)-1-hydroxyethyl]benzene-1-sulfonamide synthesis

Yield:1372452-41-9 89%

Reaction Conditions:

with Almag CRED A₁₆₁;NADP;glucose dehydrogenase in water;dimethyl sulfoxide at 30; pH=7;Enzymatic reaction;

Steps:

4.4

General procedure: Almac CRED (200 mg),NADP or NAD (10 mg), GDH (20 mg) and glucose (1.5 equiv) weremeasured into a 100 mL round bottomed flask then dissolved in0.1 M potassium phosphate buffer (pH 7, ca. 50 mL) and stirredat 30 C. Next, a solution of ketone (900-1700 mg) in DMSO(2.5-5 mL, depending on solubility) was added to the reactionand this was allowed to stir overnight under pH-stat control (pH7.0, adjusted with 1 M NaOH solution). The following day, reactionprogress was checked by 1H NMR. If not complete, additional CRED(100-200 mg), NADP or NAD (10 mg) and GDH (10 mg) wereadded and stirring was continued. This was repeated until the reactionreached completion or had stalled and would not go any further.

References:

Rowan, Andrew S.;Moody, Thomas S.;Howard, Roger M.;Underwood, Toby J.;Miskelly, Iain R.;He, Yanan;Wang, Bo [Tetrahedron Asymmetry,2013,vol. 24,# 21-22,p. 1369 - 1381]