Sodium Hydroxide → HCID 11299678, compound

HRID 1434749Notes

Reaction equation

HRID 1434749 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:12]=1)=[O:7])C>CO>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:11]2[CH:12]=[C:8]([C:6]([OH:7])=[O:5])[NH:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57435085HCID 57435085, compound

Product 1

HCID 11299678HCID 11299678, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 4.84 mmol) was added to a stirring, room temperature solution of 38 (0.2689 g, 0.968 mmol) in MeOH (2.42 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (30 min): The product was concentrated and then dissolved in 5 mL H2O. The product was extracted with EtOAc, then the aqueous layer was made acidic (pH=2) with the dropwise addition of 10% aq. HCl. 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 39 as a pale pink solid (Note: An undesired impurity has a retention time of 10.956 min by HPLC. 1H (CD3OD, 400 MHz): δ 10.89 (1H, broad s), 7.22 (2H, d, J=8.3 Hz), 7.13 (2H, d, J=8.3 Hz), 6.69 (1H, s), 6.66 (1H, s), 2.82 (2H, t, J=7.1 Hz), 2.73 (2H, t, J=7.1 Hz) ppm. 13C (CD3OD, 100 MHz): δ 164.48, 142.15, 132.49, 131.15, 129.21, 125.97, 123.60, 122.88, 116.44, 37.92, 29.70 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 37.92, 29.70; CH carbons: 131.15, 129.21, 122.88, 116.44 ppm. HPLC: 9.996 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (30 min)
  4. concentrationThe product was concentrated
  5. dissolutiondissolved in 5 mL H2O
  6. extractionThe product was extracted with EtOAc
  7. additionwith the dropwise addition of 10% aq. HCl
  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-c8e1b9b370b54807952400d04398d0b7
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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