Hydrochloric Acid → 2-(2-((3,5-Dimethoxy-4-methylbenzamido)methyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)acetic acid

HRID 1296759Notes

Reaction equation

HRID 1296759 reaction equation
C([O:8][C:9](=[O:39])[CH2:10][NH:11][C:12]1[CH:17]=[C:16]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)[CH:15]=[CH:14][C:13]=1[CH2:24][NH:25][C:26](=[O:38])[C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30]([CH3:35])=[C:29]([O:36][CH3:37])[CH:28]=1)C1C=CC=CC=1.[Li+].[OH-].Cl>C1COCC1.CO>[CH3:37][O:36][C:29]1[CH:28]=[C:27]([CH:32]=[C:31]([O:33][CH3:34])[C:30]=1[CH3:35])[C:26]([NH:25][CH2:24][C:13]1[CH:14]=[CH:15][C:16]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[CH:17][C:12]=1[NH:11][CH2:10][C:9]([OH:39])=[O:8])=[O:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69491566[2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-acetic acid benzyl ester

Product 1

HCID 694915312-(2-((3,5-Dimethoxy-4-methylbenzamido)methyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)acetic acidYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 14a (110 mg, 0.29 mmol) in a mixture of THF (3 mL) and methanol (3 drops) was added 10% LiOH (1 mL). The reaction mixture was stirred for 5 h at rt and acidified with 1 N HCl. The resulting solid was filtered, washed with water, and dried to give compound 47a (57 mg, 52%).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-3f88018816014c27919f1858a498717f
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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