HCID 67099681, compound → HCID 57983401, compound

HRID 1868683Notes

Reaction equation

HRID 1868683 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(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]([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]([OH:21])=[O:20])=[O:16])=[C:7]2[OH:26]

Participants

3

Reactant 1

HCID 67099681HCID 67099681, compound

Product 1

HCID 57983401HCID 57983401, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((8-fluoro-4,7-dihydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.21 g, 0.55 mmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=324, M−1=322. The mixture was concentrated and triturated in ether/hexane (1:10). The solid was filtered, washed with 10 mL ether/hexane (1:10), and dried under high vacuum to give 0.17 g of the product as a yellow solid. MS (m/z)=324 (M+H)+. Calculated for C15H14FNO6 323.08.

Workup

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

Sources & evidence

ORD record
ord-b05d513adfc24d30b01092622f2b6806
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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