Hydrochloric Acid → HCID 11595049, compound

HRID 1430338Notes

Reaction equation

HRID 1430338 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].[ClH:26]>CO.O>[ClH:26].[N:18]1([CH2:17][CH2:16][O:15][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]3)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11623861HCID 11623861, compound

Product 1

HCID 11595049HCID 11595049, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of ester 12 (1.02 g, 3.20 mmol) in MeOH (8 mL) was treated with a solution of NaOH (150 mg, 3.75 mmol) in water (4 mL) and heated at reflux for 3 h. After cooling to room temperature, the solution was adjusted to pH 6 with 1 M HCl and the solvent was removed under reduced pressure. The residue was dissolved in MeOH, 1 M HCl was added dropwise and the formed precipitate was collected by filtration to give 13 (727 mg, 70%) as a brown solid. Purification of the residue obtained by evaporation of the mother liquor using column filtration on silica gel (MeOH, 1% conc. HCl) provided a second batch of 13 (232 mg, 22%). 1H NMR (300 MHz, DMSO-d6): δ=3.07-3.61 (m, 6 H, 2′-H2, 3″-H2, 5″-H2), 3.76-4.06 (m, 4 H, 2″-H2, 6″-H2), 4.43 (t, J=5.0 Hz, 2 H, 1′-H2), 6.98 (dd, J=8.9, 2.3 Hz, 1 H, 6-H), 7.01 (d, J=1.8 Hz, 1 H, 3-H), 7.20 (d, J=2.3 Hz, 1 H, 4-H), 7.37 (d, J=8.9 Hz, 1 H, 7-H), 11.39 (sbr, 1 H, NH+), 11.65 (s, 1 H, NH), 12.85 (sbr, 1 H, CO2H) ppm; 13C NMR (50.3 MHz, DMSO-d6): δ=51.6 (C-3″, C-5″), 54.9 (C-2′), 62.8 (C-1′), 63.1 (C-2″, C-6″), 103.9 (C-4), 106.9 (C-3), 113.5 (C-7), 115.9 (C-6), 127.0 (C-2), 129.0 (C-3a), 133.0 (C-7a), 152.0 (C-5), 162.6 (C═O) ppm; MS (70 eV, EI): m/z (%)=290 (6) [M-Cl]+, 100 (100) [CH2N(CH2)4O]+; C15H19ClN2O4 (326.78): calcd. C, 55.13; H, 5.86; found C, 54.96; H, 5.81.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in MeOH
  5. addition1 M HCl was added dropwise
  6. filtrationthe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-c8198ca10c494bf79419da9e6ebec541
Source dataset
uspto-grants-2015_01
Patent number
US08940784B2

Reaction notes

Loading…