Water → HCID 123905854, compound

HRID 38293Notes

Reaction equation

HRID 38293 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:14][CH2:13]1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:9])[CH3:10])=[CH:4][C:3]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([S:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:20])=[O:19])[CH2:14][CH2:13]1)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 67131919HCID 67131919, compound

Product 1

HCID 123905854HCID 123905854, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the product from step (d) (244 mg), ethyl bromoacetate (0.1 ml) and potassium carbonate (185 mg) in acetone was heated under reflux for 2 days. Water was added and the mixture was extracted with diethyl ether. The organic extracts were dried (MgSO4), evaporated in vacuo and purified by chromatography (silica, petrol—ether as eluent) to give the sub-title compound (113 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. custompurified by chromatography (silica, petrol—ether as eluent)

Sources & evidence

ORD record
ord-c697b6c9d3024fd39175c86015216b66
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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