Sodium borohydride → 3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxy-N-(4-(hydroxy(phenyl)methyl)benzyl)benzenesulfonamide

HRID 1889674Notes

Reaction equation

[C:1]([C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[S:15]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[C:19]=2[OH:26])(=[O:17])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.C(O)C>[Cl:25][C:20]1[C:19]([OH:26])=[C:18]([S:15]([N:14]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([CH:1]([OH:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:36][CH:35]=2)(=[O:17])=[O:16])[CH:23]=[C:22]([Cl:24])[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(4-benzoylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide (15 mg, 0.028 mmol) in THF (0.15 mL) and ethanol (0.15 mL) at 0° C. was added sodium borohydride (4 mg, 0.11 mmol). The reaction mixture was stirred at 0° C. for 1 h. The solvents were removed in vacuo and resulting residue was purified by preparative HPLC to give the title compound (14 mg) as a white solid. MS (ESI): 527.9 (M−H2O)+.

Workup

customThe solvents were removed in vacuo
customresulting residue
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-4107f305358d4527abd8143b6e28c44a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501992B2

Reaction notes

Loading…