Potassium Carbonate → HCID 69137546, compound

HRID 1357228Notes

Reaction equation

HRID 1357228 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:20])[C:15]=2[Br:19])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C.C(OCC)(=O)C>[CH3:33][O:32][C:30](=[O:31])[CH2:29][O:20][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:21])[CH:10]=2)[C:15]=1[Br:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 69137584HCID 69137584, compound

Product 1

HCID 69137546HCID 69137546, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-carbamic acid tert-butyl ester (0.89 g, 2.5 mmol), prepared in the previous step, potassium carbonate (1.7 g, 12.5 mmol), and methyl bromoacetate (1.26 mL, 2.75 mmol) in 10 mL of DMF was stirred under nitrogen for 18 h (overnight). The reaction was diluted with ethyl acetate and extracted three times with water. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give [1-bromo-6-(tert-butoxycarbonylamino-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (1.016 g, 96%) as an off white solid, mp 96-100° C.

Workup

  1. extractionextracted three times with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-aff1387719bc4108918935624f596040
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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