Trifluoroacetic acid → N-(4-Benzylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

HRID 1889675Notes

Reaction equation

C(O)(C(F)(F)F)=O.[BH4-].[Na+].[Cl:10][C:11]1[C:12]([OH:45])=[C:13]([S:18]([N:21]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29](O)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)(=[O:20])=[O:19])[CH:14]=[C:15]([Cl:17])[CH:16]=1>C(Cl)Cl>[CH2:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:21]([CH2:37][C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)[S:18]([C:13]2[CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]([Cl:10])[C:12]=2[OH:45])(=[O:19])=[O:20])=[CH:28][CH:27]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of TFA (1 mL) at 0° C. was added sodium borohydride (14 mg, 0.037 mmol), followed by 3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxy-N-(4-(hydroxy(phenyl)methyl)benzyl)benzenesulfonamide (10 mg, 0.018 mmol) in DCM (0.5 mL). The resulting mixture was stirred at 0° C. for 0.5 h. The solvent was removed and the residue was carefully quenched by the addition of MeOH. The mixture was purified by preparative HPLC to give the title compound (6 mg) as a white solid. MS (ESI): 530.1 (M+H)+.

Workup

customThe solvent was removed
customthe residue was carefully quenched by the addition of MeOH
customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-6a4b92f394ee4be28b2732c7686f30bf
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501992B2

Reaction notes

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