Lithium Hydroxide → HCID 67354275, compound

HRID 75814Notes

Reaction equation

HRID 75814 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]=[C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29]C)=[O:28])=[O:24])[O:20][N:19]=2)=[CH:14][CH:13]=1.[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:34])[NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:22]=[C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:32])[CH3:33])[C:27]([OH:29])=[O:28])=[O:24])[O:20][N:19]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67354586Methyl 2-(3-(4-(3-(2,4-difluorophenyl) ureido)phenyl)-1,2,4-oxadiazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 67354275HCID 67354275, compoundYield 81.89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(3-(4-(3-(2,4-difluorophenyl) ureido)phenyl)-1,2,4-oxadiazole-5-carboxamido)-3-methylbutanoate was added to THF and to this 1N lithium hydroxide was added and stirred at room temperature. After completion of the reaction the solvent was evaporated and the crude product so obtained was dissolved in ethyl acetate and washed with water, brine, dried by sodium sulphate and concentrated to give a solid. The solid was then purified by column chromatography. Yield 81.89%; 1H NMR (DMSO-d6) δ: 0.96 (d, 6H, C(CH3)2), 2.20 (m, 1H, CHMe2), 4.231 (m, 1H, NHCH), 7.07 (m, 1H), 7.35 (m, 1H), 7.67 (d, 2H), 8.011 (d, 2H), 8.10 (m, 1H), 8.61 (s, 1H, NH), 9.372 (s, 1H, NH), 9.39 (s, 1H, NH), 13.025 (s, 1H, COOH); MS (m/z) 458 (M+−1).

Workup

  1. additionwas added
  2. customAfter completion of the reaction the solvent
  3. customwas evaporated

Sources & evidence

ORD record
ord-c32e882608754b5a8435d15b5c02518c
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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