Potassium Hydroxide → HCID 66574476, compound

HRID 1777367Notes

Reaction equation

[OH-].[K+].C([O:5][C:6]([C:8]1([CH2:39][O:40][CH3:41])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)=[C:28]([Cl:38])[CH:27]=4)[O:23][N:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])C>C(O)(=O)C>[Cl:38][C:28]1[CH:27]=[C:26]([C:24]2[O:23][N:22]=[C:21]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][N:11]4[CH2:12][CH2:13][C:8]([CH2:39][O:40][CH3:41])([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]4)=[CH:20][CH:19]=3)[N:25]=2)[CH:31]=[CH:30][C:29]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium hydroxide powder (85% assay, 0.394 g, 0.0060 mol) and N-methyl-N,N-dioctyloctan-1-ammonium chloride (0.02 g) are added to a solution of 1-{4-[5-(2-chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethylpiperidine-4-carboxylic acid ethyl ester (0.38 g, 0.00069 mol) in N,N′-dimethyl formamide (5 mL). The reaction mixture is stirred at 80° C. temperature for 2 hrs. It is then cooled to room temperature and acidified with 20% aqueous acetic acid solution to pH˜5-6. The precipitated solid is filtered, dried and washed with (2×5 mL) acetone. The solid mass is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane:t-butylamine, 1:8.9:0.1) to give 1-{4-[5-(2-chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]benzyl}-4-methoxymethyl-piperidine-4-carboxylic acid.

Workup

temperatureIt is then cooled to room temperature
filtrationThe precipitated solid is filtered
customdried
washwashed with (2×5 mL) acetone
customThe solid mass is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane:t-butylamine, 1:8.9:0.1)

Sources & evidence

ORD record: ord-7333efaad6df4704923f7742b93f647d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266867B2

Reaction notes

Loading…