Cesium carbonate → HCID 67495016, compound

HRID 1620385Notes

Reaction equation

HRID 1620385 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][CH2:27][C@H:28]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:29]([O:31][CH3:32])=[O:30])(=[O:25])=[O:24])=[CH:19][CH:18]=1>CC(C)=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][O:16][C:17]2[CH:18]=[CH:19][C:20]([S:23]([NH:26][CH2:27][C@H:28]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[C:29]([O:31][CH3:32])=[O:30])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 67494912HCID 67494912, compound

Product 1

HCID 67495016HCID 67495016, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

420 mg (1.3 mmol) of cesium carbonate and then 0.2 ml (1.3 mmol) of 1-bromomethyl-4-fluorobenzene are added to a solution of 400 mg (1.2 mmol) of methyl(S)-3-(4-hydroxybenzenesulfonylamino)-2-piperidin-1-ylpropanoate in 10 ml of acetone. After stirring at ambient temperature for 18 h, the reaction medium is filtered and then the filtrate is concentrated under vacuum. The crude product is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 460 mg (87%) of methyl(S)-3-[4-(4-fluorobenzyloxy)benzenesulfonylamino]-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Workup

  1. filtrationthe reaction medium is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe crude product is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-46cefdd5eba94025b1023badeca7e9c8
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

Loading…