Lithium Hydroxide → HCID 11532424, compound

HRID 2244021Notes

Reaction equation

HRID 2244021 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:36])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:35])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=3[CH2:32][CH2:33][CH3:34])[CH:15]=2)[CH:7]=1>O1CCCC1.O>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:13]([NH:12][C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[C:5]([OH:36])=[O:4])=[O:35])=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59212581HCID 59212581, compound

Product 1

HCID 11532424HCID 11532424, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 1N lithium hydroxide (30 mL) to a solution of 3-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoylamino]-benzoic acid methyl ester (4.00 g, 8.67 mmol) in tetrahydrofuran (40 mL). Stir overnight at room temperature and then dilute with water. Acidify the resulting mixture (the salt precipitated) with 1N hydrochloric acid. Concentrate to remove the organic solvents, filter and wash with water several times, then with hexanes. Dry to afford the title compound as a white powder (3.56 g, 92%): 1H NMR (DMSO-d6) δ 0.83 (t, 3H), 1.50 (sextet, 2H), 2.58 (s, 3H), 2.62 (t, 2H), 5.36 (s, 2H), 6.75 (d, 1H), 7.49 (t, 1H), 7.59 (t, 1H), 7.67 (d, 1H), 7.71 (d, 1H), 7.82 (d, 1H), 7.96 (d, 1H), 8.04 (d, 1H), 8.06 (s, 1H), 8.41 (s, 1H), 10.49 (s, 1H), 12.85 (s, 1H), 13.00 (bs, 1H); MS (APCI-neg mode) m/z (rel intensity) 446 (100).

Workup

  1. customprecipitated) with 1N hydrochloric acid
  2. concentrationConcentrate
  3. customto remove the organic solvents
  4. filtrationfilter
  5. washwash with water several times
  6. customDry

Sources & evidence

ORD record
ord-456adcb576ae48778255e6f197dd5f85
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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