Cesium carbonate → (2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester

HRID 11707Notes

Reaction equation

HRID 11707 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH2:24][C:25]([NH2:27])=[O:26])=[O:9])=[C:4]([OH:30])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>O1CCOCC1>[C:42]([O:41][C:39](=[O:40])[CH2:38][O:30][C:4]1[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[CH2:24][C:25](=[O:26])[NH2:27])=[O:9])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 69655726(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide

Product 1

HCID 69656159(2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl EsterYield 87.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide (0.070 g, 0.16 mmol), cesium carbonate (0.078 g, 0.24 mmol) and tert-butyl bromoacetate (0.038 g, 0.028 mL, 0.193 mmol) were stirred in dioxane (2 mL). After 2.5 days, the solution was filtered, concentrated and chromatographed on silica gel to yield the title compound as a white solid (0.077 g).

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-cf0e8160df2f4b5284c3b3935cb1a9cb
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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