Water → HCID 18548528, compound

HRID 1266039Notes

Reaction equation

HRID 1266039 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[O:8][C:9](=[O:28])[CH2:10][CH2:11][CH2:12]/[C:13](/[CH3:27])=[CH:14]/[C:15]1[C:20]2[NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[C:19]=2[CH:18]=[CH:17][CH:16]=1.O>CO>[CH3:27]/[C:13](=[CH:14]\[C:15]1[C:20]2[NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[C:19]=2[CH:18]=[CH:17][CH:16]=1)/[CH2:12][CH2:11][CH2:10][C:9]([OH:28])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 70009098HCID 70009098, compound

Product 1

HCID 18548528HCID 18548528, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (43.32 mmol, 5.987 g) was added to a solution of Example 161 (7.22 mmol, 2.066 g) in 200 mL MeOH (gently heated with a heat gun to get it in solution) and 100 mL H2O. The reaction mixture was stirred at rt for 24 h. The MeOH was removed in vacuo and the residue was taken up in H2O and extracted with EtOAc. The aqueous layer was made acidic (pH 0-1) using 2N HCl when the product precipitates out of solution as a white solid. The solid was filtered, washed with H2O and dried (1.878 g; 96%). The product was used without further purification: mp=257-259° C.; 1H NMR (DMSO-d6) δ 1.83-1.93 (m, 2H), 2.33 (t, 2H, J=6.0 Hz), 2.75 (t, 2H, J=6.0 Hz), 3.52-3.56 (m, 2H), 4.22 (br s, 2H), 6.34 (s, 1H), 7.07 (t, 1H, J=6.0 Hz), 7.65 (d, 1H, J=6.0 Hz), 7.75 (d, 1H, J=6.0 Hz), 8.23 (t, 1H, J=6.0 Hz), 11.98 (br s, 1H); HRMS calcd. for C15H16N2O3 (M+) 272.1161, found (M+) 272.1151.

Workup

  1. temperaturegently heated with a heat gun
  2. customThe MeOH was removed in vacuo
  3. extractionextracted with EtOAc
  4. customprecipitates out of solution as a white solid
  5. filtrationThe solid was filtered
  6. washwashed with H2O
  7. customdried (1.878 g; 96%)
  8. customThe product was used without further purification

Sources & evidence

ORD record
ord-03e545eded2f4f4dbdb43197ffd58dfe
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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