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

HRID 1296761Notes

Reaction equation

HRID 1296761 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)[CH:10]=[CH:9][C:8]=1[CH2:19][NH:20][C:21](=[O:33])[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([CH3:30])=[C:24]([O:31][CH3:32])[CH:23]=1.[Li+].[OH-].Cl>C1COCC1>[CH3:29][O:28][C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([O:31][CH3:32])[C:25]=1[CH3:30])[C:21]([NH:20][CH2:19][C:8]1[CH:9]=[CH:10][C:11]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)=[CH:12][C:7]=1[NH:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 694912553-[2-[(3,5-Dimethoxy-4-methyl-benzoylamino)-methyl]-5-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenylamino]-propionic acid methyl ester

Product 1

HCID 694916333-(2-((3,5-Dimethoxy-4-methylbenzamido)methyl)-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)propanoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 15a (89 mg, 0.19 mmol) in THF (1 mL) was added 10% LiOH (1 mL). The reaction mixture was stirred for 1 h at rt, and then acidified with 1 N HCl. This mixture was extracted with dichloromethane. The combined organic phases were dried and concentrated to give compound 54a (80 mg, 93%) as a beige foam. ESI-MS m/e 455.3 (M+1).

Workup

  1. extractionThis mixture was extracted with dichloromethane
  2. customThe combined organic phases were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-99e0d9cebc92427497ec39bea7e8497e
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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