Sodium Hydroxide → HCID 57435104, compound

HRID 1366931Notes

Reaction equation

HRID 1366931 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH2:13][CH2:14][CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]=1)=[O:7])C>CO>[CH:16]1([CH2:15][CH2:14][CH2:13][C:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[NH:9][CH:10]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435106HCID 57435106, compound

Product 1

HCID 57435104HCID 57435104, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 11.23 mmol) was added to a stirring, room temperature solution of 75 (0.56 g, 2.25 mmol) in MeOH (5.6 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (10 min). Upon cooling, the reaction solidified. The product was concentrated and H2O was added. When the product would not dissolve in H2O, EtOAc was added, followed by 10% HCl to acidify the aqueous layer. The organic was then removed, dried with Na2SO4, filtered, concentrated, and purified by preparative reverse phase HPLC with the following conditions: 30:70 H2O:CH3CN; 20 mL/min.; λ=254 nm. 76 was obtained as a fluffy white solid. (Note: An undesired impurity has a retention time of 12.073 min by HPLC). 1H (CD3OD, 400 MHz): δ 10.80 (1H, s), 6.72 (1H, s), 6.68 (1H, s), 2.43 (2H, t, J=7.6 Hz), 1.82-1.70 (3H, m), 1.64-1.46 (6H, m), 1.38-1.29 (2H), 1.14-1.02 (2H, m) ppm. 13C (CD3OD, 100 MHz): δ 164.45, 127.29, 122.45, 116.39, 41.31, 37.00, 33.73, 31.43, 27.96, 26.11 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 37.00, 33.73, 31.43, 27.96, 26.11; CH carbons: 122.45, 116.39, 41.31 ppm. HPLC: 10.977 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (10 min)
  4. temperatureUpon cooling
  5. concentrationThe product was concentrated
  6. additionH2O was added
  7. dissolutionWhen the product would not dissolve in H2O
  8. additionEtOAc was added
  9. customThe organic was then removed
  10. dry with materialdried with Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by preparative reverse phase HPLC with the following conditions
  14. custom76 was obtained as a fluffy white solid
  15. custom10.977 min.

Sources & evidence

ORD record
ord-469efd68298d4af4913789277225a866
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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