Chloromethyl pivalate → HCID 19815299, compound

HRID 465792Notes

Reaction equation

HRID 465792 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:21]([CH2:22][OH:23])=[C:20]([Cl:24])[N:19]=[C:18]3[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].C[O-].[Na+].[CH3:32][C:33]([CH3:40])([CH3:39])[C:34]([O:36][CH2:37]Cl)=[O:35]>CN(C)C=O>[CH3:32][C:33]([CH3:40])([CH3:39])[C:34]([O:36][CH2:37][O:2][C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:21]([CH2:22][OH:23])=[C:20]([Cl:24])[N:19]=[C:18]3[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)=[O:3])=[O:35]

Participants

5

Reactant 3

HCID 87885Chloromethyl pivalateHCID 10942334Sodium MethoxideHCID 19815439HCID 19815439, compound

Product 1

HCID 19815299HCID 19815299, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.25 g of 1-[(3'-carboxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole in 10 mL of dimethylformamide at 25° was added 0.17 g of sodium methoxide followed after 5 minutes by 0.45 g of chloromethyl trimethylacetate. The mixture was stirred at 25° for 4 days. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. This solution was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica gel afforded 1.38 g of the product as a glassy solid. NMR (200 MHz, CDCl3) δ7.87 (d, 1H); 7.54 (t, 1H); 7.43 (t, 1H); 7.29 (d, 1H); 7.11 (A2B2, 4H); 5.72 (s, 2H); 5.24 (s, 2H); 4.51 (s, 2H); 2.61 (t, 2H); 2.06 (br s, 1H); 1.68 (quint., 2H); 1.36 (sext., 2H); 1.17 (s, 9H); 0.88 (t, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThis solution was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ed578e201ae42839d984863d924ac7b
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Reaction notes

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