Benzyl Bromide → HCID 67099674, compound

HRID 1868675Notes

Reaction equation

HRID 1868675 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][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(#N)C>[F:1][C:2]1[C:3]([O:27][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[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 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67099681HCID 67099681, compound

Product 1

HCID 67099674HCID 67099674, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((8-fluoro-4,7-dihydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (0.29 g, 0.76 mmol, prepared in Example 23A-D) and K2CO3 (0.21 g, 1.5 mmol) in 5 mL ACN stirred at room temperature, was treated with 1-(bromomethyl)benzene (0.26 g, 1.5 mmol), and the resulting mixture was stirred for 12 hours, M+Na=492. The mixture was concentrated in vacuo and purified by column chromatography eluting with 10-30% EtOAc/hexane to give 0.27 g of the title compound as a white solid. MS (m/z)=492 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred for 12 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by column chromatography
  4. washeluting with 10-30% EtOAc/hexane

Sources & evidence

ORD record
ord-12f8b124304146549f12841e43c94ec2
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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