Acetic Acid → HCID 86756855, compound

HRID 1978809Notes

Reaction equation

HRID 1978809 reaction equation
[CH3:1][C:2]1[C:3]([NH:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([O-:20])=[O:19])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl.C(O)(=O)C>CO>[CH3:1][C:2]1[C:3]([NH:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([OH:20])=[O:19])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86756856HCID 86756856, compound

Product 1

HCID 86756855HCID 86756855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-(2-(3-methylpyridylureido)phenylacetate (1 eq.) in methanol was treated with 1 N NaOH (2 eq.). The reaction was stirred for 16 h, then acidified carefully with 1 N HCl to pH 7 then with acetic acid to pH 3. The product was filtered and washed with methanol then ether to give 4-(2-(3-methylpyridylureido)phenylacetic acid: 1H NMR (CD3SOCD3, 300 MHz, ppm) 11.97 (s, 1H), 8.64 (brs, 1H), 8.31 (s, 1H), 7.69 (m, 1H), 7.62 (d, 8.4 Hz, 2H), 7.33 (d, 8.4 Hz, 2H), 7.09 (m, 1H), 3.62 (s, 2H), 2.38 (s, 3H); m/z 286.

Workup

  1. filtrationThe product was filtered
  2. washwashed with methanol

Sources & evidence

ORD record
ord-1e5d8bdda7c44bd9a08ed6ceb7279c18
Source dataset
uspto-grants-2001_05
Patent number
US06239108B1

Reaction notes

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