Sodium Hydroxide → HCID 53482143, compound

HRID 2190165Notes

Reaction equation

[CH:1]1([C:4]2[CH:5]=[C:6]3[C:30]([C:31](=[O:34])[NH:32][CH3:33])=[C:29]([C:35]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=4)[O:28][C:7]3=[N:8][C:9]=2[N:10]([CH2:15][CH2:16][CH2:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21]CC(C)C)=[O:20])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[CH:5]=[C:6]3[C:30]([C:31](=[O:34])[NH:32][CH3:33])=[C:29]([C:35]4[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=4)[O:28][C:7]3=[N:8][C:9]=2[N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[CH2:15][CH2:16][CH2:17][C:18]([CH3:27])([CH3:26])[C:19]([OH:21])=[O:20])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To isobutyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)-2,2-dimethylpentanoate 3 (50 mg, 0.086 mmol) in MeOH (2 mL) is added NaOH (3 mL, 2M, 6.00 mmol) and the reaction is heated at 60° C. overnight. The MeOH is removed by evaporation, and the solution is acidified to pH 5. The solid is collected by filtration then purified by HPLC to give 30 mg (64% yield) of 5-[(5-Cyclopropyl-3-methylcarbamoyl-2-p-tolyl-furo[2,3-b]pyridin-6-yl)-methanesulfonyl-amino]-2,2-dimethyl-pentanoic acid 1H-NMR (DMSO-d6, 400 MHz) δ 12.05 (m, 1H), 8.49 (m, 1H), 7.74 (d, 2H, J=8 Hz), 7.55 (s, 1H), 7.36 (d, 2H, J=8 Hz), 3.65 (m, 2H), 3.16 (s, 3H), 2.83 (d, 3H, J=8 Hz), 2.43 (m, 1H), 2.38 (s, 3H), 1.48 (s, 2H), 1.38 (s, 2H), 1.04 (m, 2H), 1.00 (s, 6H), 0.7 (bm, 2H). MS-ES [M+H]+=528.21.

Workup

customThe MeOH is removed by evaporation
filtrationThe solid is collected by filtration
customthen purified by HPLC

Sources & evidence

ORD record: ord-12d6c0444b0c42359ecd6c5e671f3963
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324239B2

Reaction notes

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