Sodium Bicarbonate → 3-Bromo-4-oxo-4-thiazol-2-yl-butyric acid ethyl ester

HRID 895578Notes

Reaction equation

HRID 895578 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[CH2:34]([O:36][C:37](=[O:47])[CH2:38][CH2:39][C:40](=[O:46])[C:41]1[S:42][CH:43]=[CH:44][N:45]=1)[CH3:35].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:34]([O:36][C:37](=[O:47])[CH2:38][CH:39]([Br:1])[C:40](=[O:46])[C:41]1[S:42][CH:43]=[CH:44][N:45]=1)[CH3:35]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 68499389Ethyl 4-(2-thiazolyl)-4-oxobutyrate

Product 1

HCID 865876163-Bromo-4-oxo-4-thiazol-2-yl-butyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phenyltrimethylammonium tribromide (3.4 g, 8.91 mmol) in DCM (20 mL) is added dropwise to a solution of 4-oxo-4-thiazol-2-yl-butyric acid ethyl ester (1.9 g, 8.91 mmol) in DCM (30 mL. The mixture is stirred overnight at room temperature. 5% NaHCO3 (40 mL) is added to the mixture. The organic layer is separated and the aqueous layer is extracted with DCM (2×40 mL). The combined organic layers are dried and solvent removed. The residue is purified by column (hexanes/ethyl acetate 3:1) to give 3-bromo-4-oxo-4-thiazol-2-yl-butyric acid ethyl ester.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with DCM (2×40 mL)
  3. customThe combined organic layers are dried
  4. customsolvent removed
  5. customThe residue is purified by column (hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-da3d607cd8a644199f2b93ad184d0e44
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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