Sodium Hydroxide → HCID 68278181, compound

HRID 931441Notes

Reaction equation

HRID 931441 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][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)(=[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][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68278385HCID 68278385, compound

Product 1

HCID 68278181HCID 68278181, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reaction of benzoate 37 (213 mg, 0.53 mmol) and 2 M NaOH (10 mL) in dioxane (10 mL) gave acid 38 (160 mg, 78%) as a white solid: mp (H2O) 280-283° C.; 1H NMR δ 13.12 (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), 7.53 (dd, J=8.9, 7.7 Hz, 1H, H-5′), 7.35 (dt, J=7.7, 1.2 Hz, 1H, H-6′), 7.27-7.33 (m, 2H, H-2′, H-4′), 4.70 (s, 2H, CH2SO2), 3.79 (s, 3H, OCH3), 2.18 (s, 3H, CH3); MS m/z 388.5 (MH+, 100%). Anal. calcd for C19H17NO6S.¼H2O: C, 58.23; H, 4.50; N, 3.57. Found: C, 57.89; H, 4.37; N, 3.43%.

Sources & evidence

ORD record
ord-c14efb1fd0854dc3a75c7182868d4251
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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