Lithium Hydroxide → 3-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

HRID 1769338Notes

Reaction equation

C[O:2][C:3](=[O:32])[C:4]([CH3:31])([CH3:30])[CH2:5][C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:8]2[C:13]([C:14]=1[S:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][C:11]([O:20][CH3:21])=[CH:10][CH:9]=2.C1COCC1.[Li+].[OH-]>CO>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:7]2[C:8]3[C:13](=[CH:12][C:11]([O:20][CH3:21])=[CH:10][CH:9]=3)[C:14]([S:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[C:6]2[CH2:5][C:4]([CH3:31])([CH3:30])[C:3]([OH:32])=[O:2])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The compound from Step A was hydrolysed using 325 mL of THF, 600 mL of MeOH and 325 mL of 1.0M LiOH. The solution was heated to 80° C. for 3 h. The solution was acidified with 1N HC1 and extracted with 3×200 mL of EtOAc. The organic phase was washed with water (2×150 mL) and dried over MgSO4. The solution was evaporated to dryness to provide the title compound. m.p. 190°-191° C. Anal C, H, N: Calc. C 65.27; H 6.57; N 3.04, Found C 65.28; H 6.58; N 3.04

Workup

extractionextracted with 3×200 mL of EtOAc
washThe organic phase was washed with water (2×150 mL)
dry with materialdried over MgSO4
customThe solution was evaporated to dryness

Sources & evidence

ORD record: ord-543762c7a08b4f5b950e8befbec45852
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380850

Reaction notes

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