Cesium carbonate → Tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetate

HRID 1459424Notes

Reaction equation

HRID 1459424 reaction equation
[CH3:1][C:2]([CH3:29])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>CCOC(C)=O>[CH3:3][C:2]([CH3:29])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:25][CH:26]=3)=[O:28])=[CH:17][CH:18]=2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 54019812Tert-butyl 4-{4-[(4-hydroxybenzoyl)amino]phenyl}piperazine-1-carboxylate

Product 1

HCID 53850602Tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetateYield 108.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added N-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenyl)-4-hydroxybenzamide (0.56 g, 1.41 mmol) DMF (35 mL), Cs2CO3 (0.49 g, 1.51 nmmol) and tert-butyl bromoacetate (0.28 mL, 1.75 mmol). This mixture was stirred at ambient temperature for 18 h. The mixture was diluted with EtOAc and washed with H2O and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave 0.78 g of tert-butyl 4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylaminocarbonyl)phenoxyacetate which was used in the next step without purification.

Workup

  1. washwashed with H2O and brine
  2. customDrying
  3. filtration(MgSO4), filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-33b4d55528264d399bf75727a6447d5e
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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