Trifluoroacetic acid → N-((4-Hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868904Notes

Reaction equation

C(O)(C(F)(F)F)=O.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:16][CH:17]=2)[C:12]([CH3:25])([CH3:24])[C:11](=[O:26])[C:10]=1[C:27]([NH:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[O:28]>>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:16][CH:17]=2)[C:12]([CH3:24])([CH3:25])[C:11](=[O:26])[C:10]=1[C:27]([NH:29][CH2:30][C:31]([OH:33])=[O:32])=[O:28]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 670998621,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983575N-((4-Hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 43.9%

Procedure

TFA (2 mL) was added to 1,1-dimethylethyl N-((4-hydroxy-1,1-dimethyl-7-(3-(methyloxy)propyl)-2-oxo-naphthalen-3-yl)carbonyl)glycinate (284 mg, 680 μmol) at ambient temperature, and the reaction was stirred for 30 minutes. The resulting mixture was concentrated to give the title compound (108 mg) as a light yellow amorphous solid after purification via preparatory LC. MS m/e=362 (M+H)+. Calculated for C19H23NO6 361.15.

Workup

concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record: ord-557551b09b654a7a84ee8c3ee3b8110d
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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