Lithium hydroxide, monohydrate → 1-{4-[5-(2-Fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(piperidine-1-ylcarbamoyl)-piperidine-4-carboxylic acid

HRID 2407509Notes

Reaction equation

O.[OH-].[Li+].C([O:11][C:12]([C:14]1([C:45](=[O:53])[NH:46][N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[N:31]=[C:30]([C:32]4[CH:37]=[CH:36][C:35]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)=[C:34]([F:44])[CH:33]=4)[O:29][N:28]=3)=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1>O.O1CCCC1>[F:44][C:34]1[CH:33]=[C:32]([C:30]2[O:29][N:28]=[C:27]([C:24]3[CH:25]=[CH:26][C:21]([CH2:20][N:17]4[CH2:16][CH2:15][C:14]([C:45](=[O:53])[NH:46][N:47]5[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]5)([C:12]([OH:13])=[O:11])[CH2:19][CH2:18]4)=[CH:22][CH:23]=3)[N:31]=2)[CH:37]=[CH:36][C:35]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of lithium hydroxide monohydrate (0.031 g, 0.000735 mol) in demineralized water (2 mL) is added to a solution of 1-{4-[5-(2-fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(piperidine-1-ylcarbamoyl)-piperidine-4-carboxylic acid benzyl ester (0.165 g, 0.000245 mol) in tetrahydrofuran (10 mL). The reaction mixture is heated at 70° C. for 2 hrs. Tetrahydrofuran is removed under reduced pressure and the residue is acidified with 2N HCl (pH ˜5). The solid mass thus formed is filtered and washed with acetone (5 mL) to furnish 1-{4-[5-(2-fluoro-biphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]-benzyl}-4-(piperidine-1-ylcarbamoyl)-piperidine-4-carboxylic acid [91, MS (ES+)=584.23].

Workup

customTetrahydrofuran is removed under reduced pressure
customThe solid mass thus formed
filtrationis filtered
washwashed with acetone (5 mL)

Sources & evidence

ORD record: ord-f4f08c41394348df83fe669eab4e90ab
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809539B2

Reaction notes

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