Sodium Hydroxide → HCID 11845293, compound

HRID 1366873Notes

Reaction equation

HRID 1366873 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:12]2[CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:11]=2[NH:10][N:9]=1)=[O:7])C>CO>[CH3:16][C:15]1([CH3:17])[C:11]2[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[C:12]=2[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57561766HCID 57561766, compound

Product 1

HCID 11845293HCID 11845293, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 15.1 mmol) was added to a stirring, room temperature solution of 2 (0.6289 g, 3.02 mmol) in MeOH (7.6 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by TLC (2.5 h). The reaction was concentrated, redissolved in EtOAc and H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise until the pH=4, then the organic was removed, and the aqueous layer was extracted with EtOAc again. The combined organics were dried with Na2SO4, filtered, and concentrated. A small amount of CH2Cl2 and hexanes were added to the colored solid product, and the colored impurity was pipetted off. The remaining solid was dried to obtain 0.2371 g (43.6%) of 3 as an off-white solid. Note: The precipitation method used below appears to be the preferred protocol. 1H (CD3OD, 400 MHz): δ 2.75 (2H, t, J=6.8 Hz), 2.29 (2H, t, J=6.8 Hz), 1.29 (6H, s) ppm. 13C (CD3OD, 100 MHz): δ 166.15, 162.23, 130.46, 126.93, 47.10, 38.22, 26.62, 21.52 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 26.62; CH2 carbons: 47.10, 21.52 ppm: LCMS: 181.4 (M+1); 163.6 ((M+1)−18). HPLC: 7.538 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by TLC (2.5 h)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in EtOAc
  6. extractionH2O, and extracted with EtOAc
  7. addition10% aq. HCl was added dropwise until the pH=4
  8. customthe organic was removed
  9. extractionthe aqueous layer was extracted with EtOAc again
  10. dry with materialThe combined organics were dried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. additionA small amount of CH2Cl2 and hexanes were added to the colored solid product
  14. customThe remaining solid was dried

Sources & evidence

ORD record
ord-546c071652664311b09875592dfb19bf
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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