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Sodium Hydroxide → Sodium 3-(3-chloro-5-{5-[3-chloro-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423378
Notes
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Reaction equation

HRID 423378 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH3:25])=[C:18]([Cl:26])[CH:17]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[CH:3]=1.[OH-].[Na+:35]>C(O)C>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH3:25])=[C:18]([Cl:26])[CH:17]=4)[O:13][N:12]=3)[CH:9]=2)[N:4]([CH2:27][CH2:28][C:29]([O-:31])=[O:30])[CH:3]=1.[Na+:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59318422Ethyl 3-(3-chloro-5-{5-[3-chloro-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Product 1

HCID 67181930Sodium 3-(3-chloro-5-{5-[3-chloro-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To ethyl 3-(3-chloro-5-{5-[3-chloro-4-(propyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate (D101) (120 mg, 2.5 mmol) in ethanol (10 ml) was added 2N NaOH (2 ml) and the mixture heated at 50° C. for 30 minutes. Evaporated off the ethanol and filtered off the white solid which had precipitated out of the remaining solution. Mass of title compound obtained on drying was 85 mg. δH (400 MHz, d6-DMSO) 1.03 (3H, t), 1.77-1.86 (2H, m), 2.34 (2H, t), 4.17 (2H, t), 4.35 (2H, t), 7.40 (1H, d), 7.71-7.74 (2H, m), 7.91 (1H, d), 8.15 (1H, dd), 8.20-8.21 (2H, m). MS (ES) C22H1935Cl2N3O4 requires 459; found 460 (MH+).

Workup

  1. customEvaporated off the ethanol
  2. filtrationfiltered off the white solid which
  3. customhad precipitated out of the remaining solution

Sources & evidence

ORD record
ord-25cd83103419475c84455a7c0320e6d4
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101775B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes