Water → HCID 46940151, compound

HRID 1914833Notes

Reaction equation

HRID 1914833 reaction equation
[CH3:1][C:2]1[CH:38]=[C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:11]([C:20]4[CH:37]=[CH:36][C:23]([CH2:24][N:25]5[CH2:30][CH2:29][CH:28]([C:31]([O:33]CC)=[O:32])[CH2:27][CH2:26]5)=[CH:22][CH:21]=4)=[N:10][C:9]=3[N:4]2[N:3]=1.O.[Li+].[OH-]>C1COCC1>[CH3:1][C:2]1[CH:38]=[C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[C:12]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:11]([C:20]4[CH:37]=[CH:36][C:23]([CH2:24][N:25]5[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=[O:32])[CH2:27][CH2:26]5)=[CH:22][CH:21]=4)=[N:10][C:9]=3[N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 46940322HCID 46940322, compound

Product 1

HCID 46940151HCID 46940151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound (13-1) (1.78 g, 3.52 mmol, 1.0 eq) was dissolved in THF (35 mL) and then added H2O (35 mL) and LiOH (178 mg, 10% w/w). The reaction was stirred at room temperature for 20 hours. After that time, the THF was removed in vacuo, and the remaining solvent was diluted with additional water and the pH adjusted to 7 with dilute HCl (5% aq). The mixture was extracted with CHCl3/MeOH (4:1, ×5). The combined organic phases were dried with brine and Na2SO4, and then concentrated onto Celite in vacuo. The material was purified by silica gel chromatography by eluting with a gradient of CHCl3 to CHCl3/MeOH (1:1) to give Compound (14-1).

Workup

  1. customAfter that time, the THF was removed in vacuo
  2. additionthe remaining solvent was diluted with additional water
  3. extractionThe mixture was extracted with CHCl3/MeOH (4:1, ×5)
  4. dry with materialThe combined organic phases were dried with brine and Na2SO4
  5. concentrationconcentrated onto Celite in vacuo
  6. customThe material was purified by silica gel chromatography
  7. washby eluting with a gradient of CHCl3 to CHCl3/MeOH (1:1)

Sources & evidence

ORD record
ord-b695198a66224862b57c5c162a78dfcd
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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