1-Bromo-2-methylpropane → HCID 67099605, compound

HRID 1868677Notes

Reaction equation

HRID 1868677 reaction equation
[F:1][C:2]1[C:3]([OH:27])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:7]2[OH:26].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH:36]([CH3:38])[CH3:37]>C(#N)C>[F:1][C:2]1[C:3]([O:27][CH2:35][CH:36]([CH3:38])[CH3:37])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:7]2[OH:26]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 67099681HCID 67099681, compound

Product 1

HCID 67099605HCID 67099605, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((8-fluoro-4,7-dihydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.29 g, 0.76 mmol, see Example 23) and K2CO3 (0.21 g, 1.5 mmol) in 5 mL ACN stirred at room temperature, was treated with 1-bromo-2-methylpropane (0.52 g, 3.8 mmol). The mixture was stirred at room temperature for 12 hours. The mixture was then warmed to 80° C. and stirred for 24 hours. The mixture was concentrated in vacuo and purified by column chromatography eluting with 10-30% EtOAc/hexane to give 0.25 g of the title compound as a white solid. MS (m/z)=458 (M+Na)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. temperatureThe mixture was then warmed to 80° C.
  3. stirringstirred for 24 hours
  4. concentrationThe mixture was concentrated in vacuo
  5. custompurified by column chromatography
  6. washeluting with 10-30% EtOAc/hexane

Sources & evidence

ORD record
ord-4c3d83d023344541841a93e04caf314c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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