Water → N-[2-(3-chlorobenzoyl)-4-[(4-phenyl-2-thiazolyl)carbonyl]phenyl]-3-oxo-beta-alanine ethyl ester

HRID 1830805Notes

Reaction equation

HRID 1830805 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[O:9])=[CH:4][C:3]=1[C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1.Cl[C:31](=[O:38])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].O>C(Cl)Cl>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][C:31](=[O:38])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[O:9])=[CH:4][C:3]=1[C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[CH3:37]

Participants

5

Reactant 3

HCID 962WaterHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 22048470HCID 22048470, compound

Product 1

HCID 22048474N-[2-(3-chlorobenzoyl)-4-[(4-phenyl-2-thiazolyl)carbonyl]phenyl]-3-oxo-beta-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of intermediate (16) (0.048 mol) in DCM (200 ml) was cooled on an ice bath. 3-chloro-3-oxo-propanoic acid, ethyl ester (0.105 mol) was added dropwise. The mixture was stirred at a low temperature for 30 min, then stirred and refluxed for 1 hour and poured out into water. The organic layer was separated, washed with K2CO3 10%, dried (MgSO4), filtered and the solvent was evaporated till dryness. The product was used without further purification, yielding (quant.) N-[2-(3-chlorobenzoyl)-4-[(4-phenyl-2-thiazolyl)carbonyl]phenyl]-3-oxo-β-alanine ethyl ester (intermediate 17).

Workup

  1. temperaturewas cooled on an ice bath
  2. stirringstirred
  3. temperaturerefluxed for 1 hour
  4. customThe organic layer was separated
  5. washwashed with K2CO3 10%
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated till dryness
  9. customThe product was used without further purification

Sources & evidence

ORD record
ord-3cd725218aa94eca9ba52c9b33d2b96a
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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