HCID 67099585, compound → HCID 57983548, compound

HRID 2078095Notes

Reaction equation

HRID 2078095 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6]([OH:27])=[C:7]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[C:8](=[O:15])[C:9]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6]([OH:27])=[C:7]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[C:8](=[O:15])[C:9]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67099585HCID 67099585, compound

Product 1

HCID 57983548HCID 57983548, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((7,8-difluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.4 g, 1 mmol) in 3 mL TFA was stirred at room temperature for 30 minutes, M+1=325, M−1=324. 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 0.24 g of the product as a pale yellow solid. MS (m/z)=326 (M+H)+. Calculated for C15H13F2NO5 325.07.

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-dde28946ad664300b8f661cd6c40ad95
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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