Acetic Acid → HCID 57559701, compound

HRID 1723958Notes

Reaction equation

HRID 1723958 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[C:15]([C:17](=[O:36])[NH:18][C:19]3[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:20]=3[O:34][CH3:35])[CH:14]=[CH:13][C:12]=2[CH3:37])[CH:10]=1)=[O:5])C.O[Li].O.CC(O)=O>CO.O>[C:25]([C:23]1[CH:22]=[C:21]([NH:29][S:30]([CH3:33])(=[O:31])=[O:32])[C:20]([O:34][CH3:35])=[C:19]([NH:18][C:17]([C:15]2[CH:14]=[CH:13][C:12]([CH3:37])=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[CH:8]3)[CH:16]=2)=[O:36])[CH:24]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 11562766HCID 11562766, compound

Product 1

HCID 57559701HCID 57559701, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-imidazole-4-carboxylic acid ethyl ester (Example 3) (820 mg, 1.55 mmol) was dissolved in 5 mL of cold MeOH and a solution of 130 mg (3.10 mmol) of LiOH-H2O in 3 mL of water was added dropwise. The mixture was allowed to warm to room temperature and was then stirred for 4 h. A 1 N HOAc solution (3.2 mL) was then added and the mixture was diluted with 30 mL of water, and then was extracted with 75 mL of EtOAc. The extract was washed with water and brine, was dried with MgSO4, filtered, and concentrated to provide 631 mg (1.26 mmol, 81%) of 1-[5-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-imidazole-4-carboxylic acid.

Workup

  1. extractionwas extracted with 75 mL of EtOAc
  2. washThe extract was washed with water and brine
  3. dry with materialwas dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13c0d936cba14b598e0e89a69bc3023e
Source dataset
uspto-grants-2009_02
Patent number
US07485657B2

Reaction notes

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