Water → 3-[4-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoic acid

HRID 423370Notes

Reaction equation

HRID 423370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O.[OH-].[Na+]>O1CCOCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[CH:20][N:21]4[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[N:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59318393Ethyl 3-[4-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

Product 1

HCID 249867423-[4-(5-{5-Chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-[4-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate (D62) (1.1 g, 2.418 mmol) was dissolved in a mixture of 1,4-dioxane (100 ml) and ethanol (100 ml). Water (50.0 ml) was added followed by 2N sodium hydroxide (2.418 ml, 4.84 mmol). The mixture was stirred at RT for one and a half hours to give a single product. Evaporated off most of the solvent, acidified with glacial acetic acid, added water (50 ml) and extracted product into EtOAc (200 ml). Washed with water (30 ml) and dried over MgSO4. The solvent was evaporated off until a white precipitate was formed. The solid was filtered off and washed with ether. Mass of title compound obtained was 780 mg. δH (400 MHz, d6-DMSO) 1.38 (6H, d), 2.81 (2H, t), 4.50 (2H, t), 5.41-5.51 (1H, m), 7.07 (1H, dd), 7.36 (1H, t), 7.59 (1H, d), 7.81 (1H, d), 7.94 (1H, dd), 8.58 (1H, d), 8.96 (1H, d), 12.40 (1H, broad s). MS (ES) C21H1935ClN4O4 requires 426; found 427 (MH+).

Workup

  1. customto give a single product
  2. customEvaporated off most of the solvent
  3. additionadded water (50 ml)
  4. extractionextracted product into EtOAc (200 ml)
  5. washWashed with water (30 ml)
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated off until a white precipitate
  8. customwas formed
  9. filtrationThe solid was filtered off
  10. washwashed with ether

Sources & evidence

ORD record
ord-b254fced97d147f781677e38eeb4ff4d
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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