HCID 67099656, compound → HCID 57983553, compound

HRID 1868680Notes

Reaction equation

HRID 1868680 reaction equation
[F:1][C:2]1[C:3]([O:27][CH3:28])=[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(C)(C)C)=[O:20])=[O:16])=[C:7]2[OH:26]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:3]([O:27][CH3:28])=[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]([OH:21])=[O:20])=[O:16])=[C:7]2[OH:26]

Participants

3

Reactant 1

HCID 67099656HCID 67099656, compound

Product 1

HCID 57983553HCID 57983553, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((8-fluoro-4-hydroxy-1,1-dimethyl-7-methoxyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (92 mg, 234 μmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=338. The mixture was concentrated and then triturated in DCM/hexane (5:10). The solid was filtered, washed with 10 mL DCM/hexane (5:10), and dried under high vacuum to give 72 mg of the product as a pale yellow solid. MS (m/z)=338 (M+H)+. Calculated for C16H16FNO6 337.10.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in DCM/hexane (5:10)
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL DCM/hexane (5:10)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d3c9e866528846689476fbbc3770a8c5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…