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

HRID 423362Notes

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]([O:34]CC)=[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+]>CO>[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:14])([F:15])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

D3 (600 mg) was treated with 2 M aq. NaOH (25 ml) and MeOH (25 ml). This mixture was stirred overnight then heated to 50° C. for 6 hours. The MeOH was then evaporated and the remaining solution acidified and extracted with EtOAc (×3). The combined organic solutions were washed with brine and evaporated to give the crude residue C(302 mg) as an off-white solid. This was triturated with cold MeOH to give the title compound (162 mg) as a grey solid. δH (d6-DMSO, 400 MHz): 2.80 (2H, t), 4.46 (2H, t), 6.64 (1H, d), 7.49-7.59 (6H, m), 7.72 (1H, d), 7.85 (1H, dd), 8.22-8.25 (1H, m), 8.31-8.34 (1H, m). MS (ES): C24H16F3N3O3S requires 483; found 484 (MH+).

Workup

customThe MeOH was then evaporated
extractionextracted with EtOAc (×3)
washThe combined organic solutions were washed with brine
customevaporated
customto give the crude residue C(302 mg) as an off-white solid
customThis was triturated with cold MeOH

Sources & evidence

ORD record: ord-902289f84c424aa39241a6b3fd7eae65
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101775B2

Reaction notes

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