Citric Acid → HCID 71678385, compound

HRID 1469773Notes

Reaction equation

HRID 1469773 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6](F)[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][CH:3]=1.[OH-].[K+].C(O)(=O)C[C:26](CC(O)=O)(C(O)=O)[OH:27]>C1COCC1.CO.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:27][CH3:26])[C:5]([CH2:14][NH:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:19])[CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14797Potassium HydroxideHCID 58483442Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

Product 1

HCID 71678385HCID 71678385, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate (Intermediate-2; step-2, 1.00 g, 3.31 mmol) in THF:MeOH:H2O (2:2:1; 5 mL) was added KOH (930 mg, 16.57 mmol). The reaction mass was heated in a sealed tube at 100° C. for 3 h. The reaction mass was neutralized with citric acid and concentrated. The residue was diluted with EtOAc and was washed with water and brine. The organic layer was separated, dried, filtered and concentrated to afford 700 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 13.65 (br s, 1H), 8.08 (t, 1H), 7.29-7.26 (d, J=8.4 Hz, 1H), 7.22-7.19 (d, J=8.7 Hz, 1H), 4.25 (d, J=5.7 Hz, 2H), 3.79 (s, 3H), 1.13 (s, 9H); MS (m/z): 300.05 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc
  3. washwas washed with water and brine
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c92a8b68a5a14c679b89bb441e37ae03
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

Loading…