Lithium Hydroxide → HCID 67261679, compound

HRID 1397862Notes

Reaction equation

HRID 1397862 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8](=[O:16])[NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[CH:4]C=1C.[Li+].[OH-:21]>CO.O>[C:5]([O:21][C:8]([NH:7][C:2]1[N:1]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:16])[NH:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:17][CH:18]=1)=[O:16])([CH3:17])([CH3:6])[CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67256991HCID 67256991, compound

Product 1

HCID 67261679HCID 67261679, compoundYield 195.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

51 (7.5 g, 21.3 mmol) was dissolved in 50 ml of MeOH and 50 ml of water, LiOH (4 équivalent, 2.0 g) was added and the reaction mixture was heated to 50° C. for 2 h. The reaction mixture is concentrated and 200 ml of water are added, then extracted twice with AcOEt. The water is acidified to pH 5 with concentrated HCl 36%, then extracted twice with AcOEt. The combine organic phase are dried over Na2SO4, filtered and concentrated to afford 57 (6.74 g, 98%) as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition200 ml of water are added
  3. extractionextracted twice with AcOEt
  4. extractionextracted twice with AcOEt
  5. dry with materialThe combine organic phase are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-de47168f23b848449040183abaad19d9
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

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