HCID 68278445, compound → HCID 53213360, compound

HRID 931437Notes

Reaction equation

HRID 931437 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]([CH3:27])[CH:22]=1)(=[O:20])=[O:19]>Cl>[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]([CH3:27])[CH:22]=1)(=[O:20])=[O:19]

Participants

3

Reactant 1

HCID 68278445HCID 68278445, compound

Product 1

HCID 53213360HCID 53213360, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Reaction of benzoate 31 (217 mg, 0.56 mmol) and 6 M HCl (10 mL) gave acid 32 (173 mg, 83%) as a white solid: mp (H2O) 287-290° C.; 1H NMR δ 13.16 (br s, 1H, CO2H), 8.05 (br d, J=8.5 Hz, 2H, H-2, H-6), 7.92 (br d, J=8.5 Hz, 2H, H-3, H-5), 7.63 (br s, 1H, H-2′), 7.54-7.59 (m, 2H, H-4′, H-6′), 7.50 (t, J=7.6 Hz, 1H, H-5′), 4.65 (s, 2H, CH2SO2), 2.37 (s, 3H, CH3), 2.16 (s, 3H, CH3); MS m/z 372.6 (MH+, 100%). Anal. calcd for C19H17NO5S: C, 61.74; H, 4.61; N, 3.77. Found: C, 61.51; H, 4.56; N, 3.80%.

Sources & evidence

ORD record
ord-2b9be298968844f49222a7bff1babaea
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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