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 2078310Notes

Reaction equation

HRID 2078310 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-3bdd088ecc0b47bea33b350135c6ce00
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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