HCID 67099874, compound → HCID 54748141, compound

HRID 2078068Notes

Reaction equation

HRID 2078068 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH2:13][CH3:14])([CH3:12])[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[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]([CH2:13][CH3:14])([CH3:12])[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[C:5]2[OH:27]

Participants

3

Reactant 1

HCID 67099874HCID 67099874, compound

Product 1

HCID 54748141HCID 54748141, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((6-chloro-1-ethyl-4-hydroxy-1-methyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.4 g, 1 mmol) in 3 mL TFA was stirred at room temperature for 30 minutes, M+1=338, M−1=336. The mixture was concentrated in vacuo and the residue was sonicated in 10 mL heptane. The solid was filtered, washed with 10 mL heptane, and dried under high vacuum to give 0.27 g of the title compound as an off-white solid. MS (m/z)=338 (M+H)+. Calculated for C16H16ClNO5 337.07.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was sonicated in 10 mL heptane
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL heptane
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-8add370515ad4dd4815b03938e9d3141
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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