Lithium Hydroxide → 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

HRID 1189568Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

Ethyl 2-(2-(2-hydroxyethyl)-3,5-dimethyl-4-(4-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (20 mg, 0.045 mmol) in THF (2.0 ml), MeOH (0.500 ml) and water (0.50 ml) was stirred and LiOH (4.27 mg, 0.178 mmol) was added. The resulting mixture was stirred at 25° C. for two hours. The solvent was then removed and water was added, followed by 1 N HCl. The solvent was again removed, MeOH was added, and the resulting solution purified by preparative HPLC to give 12 mg of a light blue solid (12 mg, 0.029 mmol, 64.0% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.63 (d, 2H), 7.19 (d, 2H), 4.57 (s, 2H), 3.76 (s, 2H), 3.66 (t, 2H), 3.18-3.15 (m, 4H), 2.76-2.73 (m, 4H), 2.03 (s, 3H), 1.78 (s, 3H), 1.70-1.66 (m, 4H).

Workup

customThe solvent was then removed
additionwater was added
customThe solvent was again removed
additionMeOH was added
customthe resulting solution purified by preparative HPLC

Sources & evidence

ORD record: ord-78aa3118824d4cd684cbb70d3c1a26c9
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674115B2

Reaction notes

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