Acetic Acid → HCID 118195085, compound

HRID 1048727Notes

Reaction equation

HRID 1048727 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:6][O:5][C:4](=[O:7])[CH:3]1[S:8][CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[C:18]=1[C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1.[O:32]1CCCC1.[OH-].[Na+].C(O)(=O)C>CO.O>[OH:5][CH2:6][C:2]([CH3:31])([CH3:1])[CH:3]([S:8][CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[C:18]=1[C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=1)[C:4]([OH:7])=[O:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 90031718HCID 90031718, compound

Product 1

HCID 118195085HCID 118195085, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

130 mg (0.303 mmol) of 4,4-dimethyl-3-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methylthio)dihydrofuran-2(3H)-one were dissolved in 2 ml of methanol and 2 ml of tetrahydrofurane followed by the addition of 0.334 ml (0.334 mmol) of a 1N sodium hydroxide aqueous solution. The solution was stirred for 16 h. It was acidified down to an acid pH with acetic acid, and diluted with water until precipitation of a solid, which was then filtered and washed with water. 115 mg of 4-hydroxy-3,3-dimethyl-2-((3-((3-(trifluoromethyl)phenyl)-ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio) butanoic acid were obtained as a pale brown solid. LC-MS: m/z=447 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.69 (s, 1H), 8.77 (d, J=6.7 Hz, 1H), 8.11 (s, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.70 (t, J=8.2 Hz, 2H), 7.54-7.41 (m, 1H), 7.16 (t, J=6.6 Hz, 1H), 4.81 (d, J=12.3 Hz, 1H), 4.70 (sl, 1H), 4.58 (d, J=12.3 Hz, 1H), 3.92 (s, 1H), 3.40 (s, 1H), 3.10 (d, J=10.4 Hz, 1H), 0.86 (s, 3H), 0.82 (s, 3H)

Workup

  1. filtrationwas then filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-dd2c028e7989478bb0fc2961239b0df0
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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