Lithium Hydroxide → 3-[1-(4-Chlorobenzyl)-5-(furo[3,2-b]pyridin-5-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoic acid

HRID 1492413Notes

Reaction equation

[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[N:23]=[C:22]5[CH:24]=[CH:25][O:26][C:21]5=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31]C)=[O:30])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[N:23]=[C:22]5[CH:24]=[CH:25][O:26][C:21]5=[CH:20][CH:19]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([OH:31])=[O:30])=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 540 mg(1.1 mmol) of the ester from Step 4 in THF (11 mL) and MeOH (5.5 mL) was added aqueous LiOH 1.0N (3 mL, 3 mmol). The resulting solution was heated at 50° C. for 5 hours. The reaction was diluted with aqueous NH4OAc 25% w/v (50 mL) and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The resulting residue was purified by crystallization in EtOAc/hexane (1:4, 30 mL) to give the title compound as a white solid; m.p. 157° C. The sodium salt was prepared by dissolving the acid in ethanol, adding one equivalent of aqueous NaOH, and freeze drying the resulting solution. The sodium salts of the remaining examples were prepared in the same way.

Workup

extractionthe mixture was extracted with EtOAc
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customThe resulting residue was purified by crystallization in EtOAc/hexane (1:4, 30 mL)

Sources & evidence

ORD record: ord-38bef8b4f7c0439794a13a792398aad4
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374635

Reaction notes

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