Sodium Hydroxide → HCID 68278282, compound

HRID 931445Notes

Reaction equation

HRID 931445 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])(=[O:20])=[O:19].[OH-].[Na+]>O1CCOCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)=[N:4][C:3]=1[CH2:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278408HCID 68278408, compound

Product 1

HCID 68278282HCID 68278282, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 43 (131 mg, 0.34 mmol) and 1 M NaOH (10 mL) in dioxane (10 mL) gave acid 44 (109 mg, 83%) as a white solid: mp (H2O) 235-238° C.; 1H NMR δ 13.15 (br s, 1H, CO2H), 8.06 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.90 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.57 (d, J=8.1 Hz, 1H, H-6′), 7.28 (br s, 1H, H-3′), 7.17 (br d, J=8.1 Hz, 1H, H-5′), 4.61 (s, 2H, CH2SO2), 2.56 (s, 3H, CH3), 2.33 (s, 3H, CH3), 2.16 (s, 3H, CH3); MS m/z 386.5 (MH+, 100%). Anal. calcd for C20H19NO5S.¾H2O: C, 62.69; H, 5.50; N, 3.32. Found: C, 62.52; H, 5.27; N, 3.48%.

Sources & evidence

ORD record
ord-ef8738ac44174f44b0ab5067feb864df
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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