Hydrochloric Acid → 3-[3-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzoic acid

HRID 2267032Notes

Reaction equation

[OH-].[Li+].C[O:4][C:5](=[O:34])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=3[CH2:31][CH2:32][CH3:33])[CH:14]=2)[CH:7]=1.Cl>C(O)(C)C>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][C:15]2[CH:14]=[C:13]([NH:12][C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=3)[C:5]([OH:34])=[O:4])[CH:18]=[CH:17][CH:16]=2)=[C:22]([CH2:31][CH2:32][CH3:33])[C:23]=1[OH:30])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

Add 1M aqueous lithium hydroxide (3.23 mL, 3.23 mmol) to a solution of 3-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenylamino]-benzoic acid methyl ester (280 mg, 0.646 mmol) in isopropanol (25 mL) and stir. Heat to 80° C. After 1 hour, pour reaction into 1N aqueous hydrochloric acid (50 mL) and extract with ethyl acetate. Combine organic layers, dry with sodium sulfate, filter and concentrate to dryness. Purify the resulting residue by trituration (ether:hexanes) to yield the title compound as a yellow solid (200 mg, 74%): 1H NMR (DMSO-d6) δ 0.81 (t, 3H), 1.46 (sextuplet, 2H), 2.58 (m, 5H), 5.23 (s, 2H), 6.71 (d, 1H), 6.94 (d, 1H), 7.02 (d, 1H), 7.19 (s, 1H), 7.29 (m, 3H), 7.40 (d, 1H), 7.65 (s, 1H), 7.81 (d, 1H), 8.44 (s, 1H), 12.73-12.92 (bs, 1H), 12.84 (s, 1H); MS (esi negative) m/z (rel intensity) 418 (100).

Workup

additionpour
extractionextract with ethyl acetate
dry with materialCombine organic layers, dry with sodium sulfate
filtrationfilter
concentrationconcentrate to dryness
customPurify the resulting residue by trituration (ether:hexanes)

Sources & evidence

ORD record: ord-eabd9250b9094978af58b7da6e5a8443
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858646B2

Reaction notes

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