Lithium hydroxide, monohydrate → 3-((3-(5-(Benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acid

HRID 2067563Notes

Reaction equation

HRID 2067563 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([O:27]CC)=[O:26])[C:17]2=[O:33])=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([OH:27])=[O:26])[C:17]2=[O:33])=[N:13][C:12]=1[CH3:34])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59481231Ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate

Product 1

HCID 594812233-((3-(5-(Benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-((3-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)benzoate (0.093 g, 0.19 mmol) in tetrahydrofuran (5 mL) and water (2.5 mL) was added lithium hydroxide monohydrate (0.032 g, 0.77 mmol) at ambient temperature. The resulting reaction mixture was heated to reflux for 14 hours. The solvent was removed in vacuo, and the residue was neutralized to pH 3-4 with 10% hydrochloric acid solution. The resulting precipitate was filtered, washed with water (30 mL), hexane (30 mL) and dried to afford the title compound as a colorless solid in 97% yield (0.083 g): mp 120-123° C. (water); 1H NMR (300 MHz, DMSO-d6) δ 13.10 (br s, 1H), 8.49 (t, J=6.0 Hz, 1H), 7.91-7.88 (m, 2H), 7.40-7.38 (m, 2H), 7.32-7.16 (m, 5H), 4.48 (s, 2H), 4.35-4.33 (m, 2H), 4.01-3.96 (m, 2H), 3.48-3.42 (m, 2H), 2.44 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 167.5, 162.2, 157.8, 155.6, 151.3, 142.0, 140.1, 130.4, 130.1, 128.7, 128.2, 127.6, 127.1, 118.3, 47.1, 43.0, 42.4, 42.2, 17.5; MS (ES+) m/z 451.2 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 14 hours
  4. customThe solvent was removed in vacuo
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water (30 mL), hexane (30 mL)
  7. customdried

Sources & evidence

ORD record
ord-ac9a0edf80694e8a9876d0cbfa773d24
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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