HCID 178451293, compound → HCID 57983434, compound

HRID 2078084Notes

Reaction equation

HRID 2078084 reaction equation
[F:1][C:2]1[C:3]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9]([OH:14])=[C:8]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])[C:7]2=[O:26]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[C:3]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])=[C:7]2[OH:26]

Participants

3

Reactant 1

HCID 178451293HCID 178451293, compound

Product 1

HCID 57983434HCID 57983434, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((8-fluoro-2-hydroxy-1,1-dimethyl-4-oxo-7-((phenylmethyl)oxyl)-naphthalene-3-yl)carbonyl)glycinate (0.21 g, 447 μmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=414. 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 0.16 g of a pale yellow solid. LCMS showed about 10% of debenzylated product. The product was further purified by column chromatography eluting with 1:10:100 TFA/MeOH/DCM to give 108 mg of the pure compound. MS (m/z)=414 (M+H)+. Calculated for C22H20FNO6 413.13.

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-5a12d3ec4752422e9161abcb00a083db
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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