Trifluoroacetic acid → N-((6-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alanine

HRID 2078211Notes

Reaction equation

HRID 2078211 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][C@H:18]([C:20]([O:22]C(C)(C)C)=[O:21])[CH3:19])=[O:16])=[C:5]2[OH:27].C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][C@H:18]([C:20]([OH:22])=[O:21])[CH3:19])=[O:16])=[C:5]2[OH:27]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099883HCID 67099883, compound

Product 1

HCID 57983372N-((6-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alanineYield 80.2%

Procedure

To 1,1-dimethylethyl N-((6-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alaninate (320 mg, 812 μmol) was added TFA (2 mL) at ambient temperature. The mixture was stirred for 30 minutes and was then concentrated, precipitated with hexanes, filtered, washed, and dried in a vacuum oven to give the title compound (220 mg) as a white solid. MS (m/z)=338 (M+H)+. Calculated for C16H16ClNO5 337.07.

Workup

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

Sources & evidence

ORD record
ord-24216a30ebda49d09ead7a8055d64eea
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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