Ethyl chloroacetate → (3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid ethyl ester

HRID 1710647Notes

Reaction equation

HRID 1710647 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:27])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([OH:25])=[CH:24][C:19]=4[O:18][C:17]3=[O:26])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:28][CH3:29].Cl[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][O:25][C:23]1[CH:22]=[CH:21][C:20]2[N:16]([CH2:15][C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:28][CH3:29])[CH:4]=4)[CH2:13][CH2:12]3)=[O:27])[C:17](=[O:26])[O:18][C:19]=2[CH:24]=1)[CH3:36]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 10796Cesium carbonateHCID 588343493-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one

Product 1

HCID 58834369(3-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-6-hydroxy-3H-benzooxazol-2-one (44) (300 mg, 0.72 mmol, 1 eq), ethyl chloroacetate (132 mg, 1.08 mmol, 1.5 eq), cesium carbonate (467 mg, 1.43 mmol, 2 eq) in DMF (2 ml) was stirred at rt overnight. The reaction mixture was diluted with ethyl acetate, washed with water, and purified by flash chromatography to provide (3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazol-6-yloxy)-acetic acid ethyl ester (45).

Workup

  1. washwashed with water
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-d272a808bf6245e48cb11ebdf16f2287
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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