1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate → N-((4-Hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868902Notes

Reaction equation

HRID 1868902 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[C:5]([CH3:18])([CH3:17])[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])=[CH:9][CH:10]=2)[C:5]([CH3:17])([CH3:18])[C:4](=[O:19])[C:3]=1[C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Participants

3

Reactant 1

HCID 670998541,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983559N-((4-Hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 23.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-((1E)-3-(methyloxy)-1-propen-1-yl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate (75 mg, 181 μmol) was dissolved in TFA (2 mL) at ambient temperature for 30 minutes before it was concentrated, precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (15 mg) as a yellow solid. MS m/e=360 (M+H)+. Calculated for C19H21NO6 359.14.

Workup

  1. concentrationwas concentrated
  2. customprecipitated with hexanes
  3. filtrationfiltered
  4. washwashed with hexanes
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-820f104439a746b8bbd8cd91314657b5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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