Ethyl bromoacetate → HCID 90022701, compound

HRID 1754844Notes

Reaction equation

HRID 1754844 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[S:15][CH:16]=1)=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CC(C)=O.O>[CH2:33]([O:32][C:30](=[O:31])[CH2:29][O:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[C:7](=[O:8])[NH:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[S:15][CH:16]=1)[CH3:34]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 90021697HCID 90021697, compound

Product 1

HCID 90022701HCID 90022701, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-chloro-2-hydroxy-N-[2-(2-isopropyl-thiazol-4-yl)-ethyl]-benzamide (400 mg, 1.23 mmol, 1.00 eq.) and potassium carbonate anhydrous (340 mg, 2.46 mmol, 2.00 eq.) in acetone (20 mL), ethyl bromoacetate (0.14 mL, 1.29 mmol, 1.05 eq.) was added. The mixture was stirred at r.t. for 5 hours. The reaction mixture was poured in water (50 mL). The mixture was extracted with AcOEt (2×20 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by flashmaster (column: 25 g, flow: 30 mL/min, 45 fractions of 15 mL, Heptane+20% AcOEt to Heptane+80% AcOEt) to yield the ester as a white solid.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with AcOEt (2×20 mL)
  3. dry with materialphases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flashmaster (column: 25 g, flow: 30 mL/min, 45 fractions of 15 mL, Heptane+20% AcOEt to Heptane+80% AcOEt)

Sources & evidence

ORD record
ord-03b08357c90f4ac48df36d4ea2b2c5e3
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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