Methanol → HCID 19815381, compound

HRID 466436Notes

Reaction equation

HRID 466436 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([O:36]C)=[O:35])=[CH:23][CH:22]=2)[C:7]([CH2:11][NH:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CO>O>[CH2:1]([C:5]1[N:6]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:38])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([OH:36])=[O:35])=[CH:23][CH:22]=2)[C:7]([CH2:11][NH:12][S:13]([C:16]([F:17])([F:18])[F:19])(=[O:14])=[O:15])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19815444HCID 19815444, compound

Product 1

HCID 19815381HCID 19815381, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Butyl-1-[4-(2-carbomethoxybenzoyl)benzyl]-4-chloro-5-[(trifluoromethylsulfonamido)methyl]imidazole (150 mg, 0.26 mmol, 1 eq), 1.000N NaOH (0.55 mL, 0.55 mmol, 2.1 eq), methanol (20 mL), and water (0.5 mL) were mixed and stirred for 5 hours at room temperature under N2. The solvent was removed in vacuo. Water (50 mL) was added and the pH was adjusted to 4 with 1N HCl. Tan solids precipitated. These were collected and dried to yield 89 mg. NMR (200 MHz, DMSO-d6) δ 7.98 (d, 1H, J=7 Hz); 7.70 (t, 1H, J=7 Hz); 7.68 (t, 1H, J=7 Hz); 7.63 (d, 2H, J=10 Hz); 7.37 (d, 1H, J=7 Hz); 7.10 (d, 2H, J=10 Hz); 5.34 (s, 2H); 4.20 (s, 2H); 2.50 (t, 2H, J=7 Hz); 1.49 (t of t, 2H, J=7,7 Hz); 1.27 (t of q, 2H, J=7,7 Hz); 0.80 (t, 3H, J=7 Hz). Mass calcd. for C24H23ClF3N3O5S: 557.0999. Found: 557.0988

Workup

  1. customThe solvent was removed in vacuo
  2. additionWater (50 mL) was added
  3. customTan solids precipitated
  4. customThese were collected
  5. customdried
  6. customto yield 89 mg

Sources & evidence

ORD record
ord-7ab3483299df450ca95608f000bce37d
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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