Sodium Hydroxide → HCID 11845295, compound

HRID 1434730Notes

Reaction equation

HRID 1434730 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:12]2[CH2:13][CH2:14][CH:15]([CH3:16])[C:11]=2[NH:10][N:9]=1)=[O:7])C>CO>[CH3:16][CH:15]1[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 44118220HCID 44118220, compound

Product 1

HCID 11845295HCID 11845295, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 5.02 mmol) was added to a stirring, room temperature solution of 5 (0.1949 g, 1.00 mmol) in MeOH (12.5 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by TLC (0.5 h). The reaction was concentrated and then dissolved in 2 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 0.1223 g (73.3%) of 6. 1H (CD3OD, 400 MHz): δ 3.18-3.07 (1H, m), 2.84-2.62 (3H, m), 2.08-1.96 (1H, m), 1.25 (3H, d, J=6.8 Hz) ppm. 13C (CD3OD, 100 MHz): δ 164.49, 163.43, 131.67, 129.41, 40.87, 33.40, 23.61, 19.73 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 19.73; CH2 carbons: 40.87, 23.61; CH carbons: 33.40 ppm. HPLC: 7.006 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by TLC (0.5 h)
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 2 mL H2O
  6. addition10% aq. HCl was added dropwise until the pH=2
  7. customThe white solid that precipitated from the reaction
  8. filtrationwas filtered off
  9. washwashed with cold H2O
  10. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-37a2876ec43c4e0ab6f9bbb818e052c0
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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