Isopropanol → HCID 57435081, compound

HRID 1366894Notes

Reaction equation

HRID 1366894 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[NH:9][C:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:12]=1)=[O:7])C.CC(O)C>CO>[CH2:13]([C:10]1[NH:9][C:8]([C:6]([OH:7])=[O:5])=[CH:12][CH:11]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 14449695HCID 14449695, compound

Product 1

HCID 57435081HCID 57435081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Freshly prepared aq. NaOH (10 M in H2O, 1.67 mmol) was added to a stirring, room temperature solution of 35 (0.0814 g, 0.333 mmol) in MeOH (0.83 mL, 0.4 M) under N2. 0.4 mL of iPrOH was added to solubilize 35. The reaction was heated to reflux until the reaction was judged complete by HPLC. The product was concentrated and then dissolved in 1.9 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 36 as a pale pink solid (Note: An undesired impurity has a retention time of 12.055 min by HPLC. Also, the 13C NMR of 36 at room temperature showed doublets for the peaks corresponding to the pyrrole carbons, benzyl carbon, and acid carbon. When the NMR probe was heated to 28° C., all doubled peaks collapsed into single peaks as reported below. 1H (CD3OD, 400 MHz): δ 10.97 (1H, broad s), 7.25-7.20 (2H, m), 7.18-7.11 (3H, m), 6.76 (1H, d, J=3.4 Hz), 5.90 (1H, d, J=3.4 Hz), 2.94-2.84 (4H, m) ppm. 13C (CD3OD, 100 MHz): δ 164.51, 142.68, 139.79, 129.40, 129.30, 126.98, 122.36, 117.47, 108.90, 37.00, 30.67 ppm. DEPT (CDCl3, 100 MHz): CH2 carbons: 37.00, 30.67; CH carbons: 129.40, 129.30, 126.98, 117.47, 108.90 ppm. HPLC: 11.239 min.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until the reaction
  3. concentrationThe product was concentrated
  4. dissolutiondissolved in 1.9 mL H2O
  5. addition10% aq. HCl was added dropwise until the pH=2
  6. customThe white solid that precipitated from the reaction
  7. filtrationwas filtered off
  8. washwashed with cold H2O
  9. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-a30b4821d660471baeced8de967670f2
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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