Sodium Hydroxide → HCID 11845654, compound

HRID 1366907Notes

Reaction equation

HRID 1366907 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[NH:10][N:9]=1)=[O:7])C>CO>[CH3:17][C:16]([CH3:18])=[CH:15][CH2:14][CH2:13][C:11]1[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435093HCID 57435093, compound

Product 1

HCID 11845654HCID 11845654, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 11.85 mmol) was added to a stirring, room temperature solution of 50 (0.0.5269 g, 2.37 mmol) in MeOH (5.9 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (5 min): The reaction was concentrated, redissolved in H2O, and extracted with EtOAc. 10% aq. HCl was added dropwise to the aqueous layer 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 0.4034 g (87.6%) of 51. 1H (CD3OD, 400 MHz): δ 6.56 (1H, s), 5.14 (1H, t), 2.68 (2H, t, J=7.3 Hz), 2.33 (2H, q, J=7.3 Hz), 1.67 (3H, s), 1.56 (3H, s) ppm. 13C (CD3OD, 100 MHz): δ 164.94, 148.55, 143.23, 123.94, 107.32, 28.89, 27.04, 25.85, 17.69 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 25.85, 17.69; CH2 carbons: 28.89, 27.04; CH carbons: 123.94, 107.32 ppm: HPLC: 8.475 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (5 min)
  4. concentrationThe reaction was concentrated
  5. dissolutionredissolved in H2O
  6. extractionextracted with EtOAc
  7. addition10% aq. HCl was added dropwise to the aqueous layer until the pH=2
  8. customThe white solid that precipitated from the reaction
  9. filtrationwas filtered off
  10. washwashed with cold H2O
  11. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-63ec2ea0cc504130ba83a63e7287454a
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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