Methanol → HCID 68334570, compound

HRID 2403232Notes

Reaction equation

HRID 2403232 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:3]=1OC.[Li+].[OH-:22].[CH3:23][OH:24]>O>[C:5]([O:22][C:23]([NH:1][C:2]1[CH:3]=[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:24])([CH3:17])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 67257562HCID 67257562, compound

Product 1

HCID 68334570HCID 68334570, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

50 (7.5 g, 21.3 mmol) was dissolved in 50 ml of MeOH and 50 ml of water, LiOH (4 equivalent, 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 3 with concentrated HCl 36%, then extracted twice with AcOEt. The combine organic phase are dried over Na2SO4, filtered and concentrated to afford 56 (6.81 g, 99%) 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-7469cb7ba38e477f90fc1a4295df33b7
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

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