Acetic Acid → 4-{[3-(3-Amino-propoxy)-phenyl]-hydroxy-phenyl-methyl}-benzoic acid

HRID 574061Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([C:26]2[CH:31]=[CH:30][C:29](C3OCC(C)(C)N=3)=[CH:28][CH:27]=2)([OH:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=1)(C)(C)C.C[C:41]([OH:43])=[O:42]>CO.C(Cl)(Cl)Cl>[NH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([C:18]([OH:25])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:26]2[CH:31]=[CH:30][C:29]([C:41]([OH:43])=[O:42])=[CH:28][CH:27]=2)[CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 75 °C

Procedure

In a 50 mL round bottomed flask placed with [3-(3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenoxy)-propyl]-carbamic acid tert-butyl ester (3, 220 mg) was added 3 mL of 80% aqueous AcOH and the reaction mixture was heated 75° C. for overnight. Then the reaction mixture was concentrated and dried and added 3 mL of 20% NaOH/EtOH (1:1, v/v) and refluxed for 3 h. Residue obtained on evaporation of the solvent was dissolved in CH3OH/CHCl3 mixture and adsorbed with silica gel and dried. The dried silica gel with compound was purified by silica gel column already flashed with 1% NH4OH in Et2O solution. Elution of the column at 50% CH3OH/CH2Cl2 gave 4-{[3-(3-Amino-propoxy)-phenyl]-hydroxy-phenyl-methyl}-benzoic acid, 4 as a colorless gelly solid. Yield: 96%. Mass: 378 (MH+), 376 (M-H), 360 (M-OH).

Workup

concentrationThen the reaction mixture was concentrated
customdried
additionadded 3 mL of 20% NaOH/EtOH (1:1
temperaturev/v) and refluxed for 3 h
customResidue obtained on evaporation of the solvent
customdried
customThe dried silica gel with compound was purified by silica gel column
washElution of the column at 50% CH3OH/CH2Cl2

Sources & evidence

ORD record: ord-7d357d56b15a445b875fbd8b642ecd98
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034798B2

Reaction notes

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