Lithium hydroxide, monohydrate → 2-(3-cyano-2-cyclopropyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid
Reaction equation
[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([O:27]CC)=[O:26])[C:4]=1[CH:30]1[CH2:32][CH2:31]1)#[N:2].O.[OH-].[Li+]>>[C:1]([C:3]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)(=[O:17])=[O:16])=[C:6]([CH3:23])[N:5]([CH2:24][C:25]([OH:27])=[O:26])[C:4]=1[CH:30]1[CH2:31][CH2:32]1)#[N:2]Participants
3
Procedure
was followed using ethyl 2-(3-cyano-2-cyclopropyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (65.4 mg, 0.144 mmol) and lithium hydroxide hydrate (12.05 mg, 0.287 mmol) to afford 2-(3-cyano-2-cyclopropyl-5-methyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid as a white solid (58.5 mg, 0.137 mmol, 95% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.94 (d, 1H), 7.43 (dd, 1H), 7.32 (dd, 1H), 7.08 (d, 1H), 4.69 (s, 2H), 4.26 (s, 2H), 3.31-3.35 (m, 4H), 1.90-1.95 (m, 7H), 1.65 (m, 1H), 0.86-0.97 (m, 4H).
Sources & evidence
- ORD record
- ord-3699eb584ca24393803f8f369eebb64a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674115B2
Reaction notes
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