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Sodium Hydroxide → Sodium 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propionate

HRID 423363
Notes
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Reaction equation

HRID 423363 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+:36]>CCOC(C)=O.O>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH2:30][CH2:31][C:32]([O-:34])=[O:33])[CH:25]=[CH:24]5)[N:17]=3)[S:10][C:11]=2[C:12]([F:14])([F:15])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 248247243-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoic acid

Product 1

HCID 59318357Sodium 3-(5-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

E1 (30 mg) was dissolved in EtOAc (1 ml), treated with 2M aqueous NaOH (40 ul), diluted with H2O (1 ml) and extracted with EtOAc (3×5 ml), using a small volume of brine during the third extraction to aid phase separation. The combined organics were evaporated to give the title compound (37 mg) as a green solid. δH (methanol-d4, 400 MHz): 2.68 (2H, t), 4.48 (2H, t), 6.55 (1H, d), 7.49 (1H, d), 7.45-7.56 (5H, m), 7.62 (1H, d), 7.92 (1H, d), 8.03 (1H, s), 8.35 (1H, s). MS (ES+): C24H16F3N3O3S requires 483; found 484 (MH+).

Workup

  1. extractionextracted with EtOAc (3×5 ml)
  2. extractionduring the third extraction
  3. customphase separation
  4. customThe combined organics were evaporated

Sources & evidence

ORD record
ord-bc392754c4fe456f822a499fde0ceab0
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes