Potassium Carbonate → HCID 67056360, compound

HRID 1777277Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

270 mg (1.9 mmol) of potassium carbonate then 380 mg (1.9 mmol) of 4-chloromethyl-2-methylquinoline and 15 mg of potassium iodide are added to a solution of 500 mg (1.6 mmol) of methyl (S)-3-(4-hydroxybenzoyl-amino)-2-piperidin-1-ylpropanoate in 15 ml of 2-butanone. The reaction medium is stirred at 80° C. for 18 h. After filtration, the filtrate is concentrated under vacuum. The crude product is purified by chromatography over silica gel eluted with a 50/50 heptane/ethyl acetate mixture. 620 mg (83%) of methyl (S)-3-[4-(2-methylquinolin-4-ylmethoxy)benzoylamino]-2-piperidin-1-ylpropanoate are obtained in the form of a yellow solid.

Workup

filtrationAfter filtration
concentrationthe filtrate is concentrated under vacuum
customThe crude product is purified by chromatography over silica gel
washeluted with a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-1189155c83b74a59ba5fb527b1459cc0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266848B2

Reaction notes

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