Hydrochloric Acid → 2-(Benzyloxymethyl)-4,6-dihydroxy-N-phenylbenzamide

HRID 505652Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10]1[CH:24]=[C:23]([O:25]COC)[CH:22]=[C:21]([O:29]COC)[C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([O:8][CH2:9][C:10]1[CH:24]=[C:23]([OH:25])[CH:22]=[C:21]([OH:29])[C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The above-obtained 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)-N-phenylbenzamide (18 mg, 0.043 mmol) was dissolved in ethanol (4 mL) and the obtained solution was added with concentrated hydrochloric acid (0.10 mL) followed by stirring at 60° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain Compound 1 (14 mg, 92%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record: ord-3fbc4d1e4f7a43dba3c322285dfe25ee
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781485B2

Reaction notes

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