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 423378Notes

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]

Participants

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

customEvaporated off the ethanol
filtrationfiltered off the white solid which
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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