Cesium carbonate → HCID 67494920, compound

HRID 1620386Notes

Reaction equation

HRID 1620386 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][C@H:31]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[C:32]([O:34][CH3:35])=[O:33])(=[O:28])=[O:27])=[CH:22][CH:21]=1>CC(C)=O>[CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[CH2:8][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:29][CH2:30][C@H:31]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[C:32]([O:34][CH3:35])=[O:33])(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 703202-BromomethylnaphthaleneHCID 67494912HCID 67494912, compound

Product 1

HCID 67494920HCID 67494920, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

420 mg (1.3 mmol) of cesium carbonate, followed by 280 mg (1.3 mmol) of 2-bromomethylnaphthalene, are added to a solution of 400 mg (1.2 mmol) of methyl(S)-3-(4-hydroxybenzenesulfonylamino)-2-piperidin-1-ylpropanoate (prepared as described in 3.1) in 10 ml of acetone. The reaction medium is stirred at ambient temperature for 18 h and then filtered. The filtrate is concentrated under vacuum and purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 420 mg (80%) of methyl(S)-3-[4-(naphthalen-2-ylmethoxy)benzenesulfonylamino]-2-piperidin-1-ylpropanoate are obtained in the form of a white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under vacuum
  3. custompurified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-12cbd575373f4738b57a7ebddee4512d
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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