Sodium Hydroxide → HCID 68278267, compound

HRID 931439Notes

Reaction equation

HRID 931439 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[O:16][C:17]=2[CH3:18])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278359HCID 68278359, compound

Product 1

HCID 68278267HCID 68278267, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 34 (285 mg, 0.71 mmol) and 2 M NaOH (10 mL) in dioxane (10 mL) gave acid 35 (246 mg, 89%) as a white solid: mp (H2O) 245-248° C.; 1H NMR [(CD3)2SO] δ 13.16 (br s, 1H, CO2H), 8.05 (dd, J=8.6, 1.8 Hz, 2H, H-2, H-6), 7.93 (dd, J=8.6, 1.8 Hz, 2H, H-3, H-5), 7.70 (ddd, J=9.0, 2.9, 2.0 Hz, 2H, H-2′, H-6′), 7.13 (ddd, J=9.0, 2.9, 2.0 Hz, 2H, H-3′, H-5′), 4.61 (s, 2H, CH2SO2), 3.84 (s, 3H, OCH3), 2.14 (s, 3H, CH3); MS m/z 388.5 (MH+, 100%). Anal. calcd for C19H17NO6S: C, 58.91; H, 4.42; N, 3.62. Found: C, 58.86; H, 4.22; N, 3.54%.

Sources & evidence

ORD record
ord-3ea1a21fa3a04e5f8e54473393f63535
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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