Lithium borohydride → N-(4-cyano-2-hydroxymethyl-benzyl)-N-(3,5-dimethyl-pyridin-2-ylmethyl)-2-nitro-benzene-sulfonamide

To a solution of 5-cyano-2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(2-nitro-benzenesulfonyl)-amino]-methyl}-benzoic acid methyl ester (0.83 g, 1.68 mmol) dissolved in THF (30 mL) and MeOH (10 mL), LiBH4 (0.37 g, 16.8 mmol) was slowly added. The mixture was stirred at room temperature for 3 hours. The mixture was concentrated in vacuo and redissolved in CH2Cl2 (50 mL). Water (50 mL) was added and the resulting mixture was extracted with CH2Cl2 (4×50 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to give crude N-(4-cyano-2-hydroxymethyl-benzyl)-N-(3,5-dimethyl-pyridin-2-ylmethyl)-2-nitro-benzene-sulfonamide (0.82 g, 78%) as a yellow foam. 1H NMR (CDCl3) δ 2.16 (s, 3H), 2.25 (s, 3H), 4.58 (s, 2H), 4.67 (s, 2H), 4.76 (br s, 1H), 4.88 (s, 2H), 7.10 (s, 1H), 7.36 (m, 2H), 7.50 (m, 1H), 7.65-7.72 (m, 3H), 7.80 (s, 1H), 7.89 (d, 1H, J=7.5 Hz).

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionredissolved in CH2Cl2 (50 mL)
3. additionWater (50 mL) was added
4. extractionthe resulting mixture was extracted with CH2Cl2 (4×50 mL)
5. dry with materialThe combined organic extracts were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-876ce87c192548189703d3d678fb68fc

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07291631B2