Bromomethyl acetate → HCID 69585023, compound

HRID 2212435Notes

Reaction equation

HRID 2212435 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]([CH3:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:22])[CH:16]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Cs+].[C:29]([O:32][CH2:33]Br)(=[O:31])[CH3:30]>CC(C)=O>[C:29]([O:32][CH2:33][O:12][C:11](=[O:13])[C:10]([NH:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH3:23])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:22])[CH:16]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 68536Bromomethyl acetateHCID 2734983Cesium bicarbonateHCID 21964610HCID 21964610, compound

Product 1

HCID 69585023HCID 69585023, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
44 °C

Procedure

To a suspension of compound 102 (170 mg, 0.5 mmol) and cesium bicarbonate (99 mg, 0.5 mmol) in acetone was added bromomethyl acetate (170 mg, 0.5 mmol) and the mixture stirred at 44° C. temperature for 16 h. After removing the solvent under reduced pressure, the residue was partitioned between ethyl acetate and 10% citric acid. The organic layer was separated, dried over MgSO4 and concentrated to afford the crude product, which was used in the next reaction without further purification.

Workup

  1. customAfter removing the solvent under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 10% citric acid
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d6ee262a95a478aac51fc9316be571f
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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