Sodium Hydroxide → HCID 91513166, compound

HRID 1242812Notes

Reaction equation

HRID 1242812 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([CH2:9][OH:10])[N:6]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH2:5]1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[OH-].[Na+]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:18][C:13]([C:11]([N:6]2[CH2:5][C:4](=[N:3][O:2][CH3:1])[CH2:8][C@H:7]2[CH2:9][O:10][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:12])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 58585503HCID 58585503, compound

Product 1

HCID 91513166HCID 91513166, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of alcohol (2) (EZ mixture, 58 mg, 0.18 mmol) and tert-butyl bromoacetate (530 μl, 3.6 mmol) in dichloromethane (0.2 ml) were added 50% aqueous NaOH (0.8 ml) and tetrabutylammonium chloride (50 mg, 0.18 mmol) at room temperature, and the whole reaction mixture was stirred for 1 hour. After dilution with water, the mixture was extracted with ethyl acetate, organic phase was washed with brine, dried (MgSO4) and concentrated. The product (compound 5) was purified by silica gel column chromatography using DCM:MeOH, 95:5 as eluant.

Workup

  1. customthe whole reaction mixture
  2. extractionAfter dilution with water, the mixture was extracted with ethyl acetate, organic phase
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe product (compound 5) was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-667fa2ba9ac34ae89a5f3d234d79414a
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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