Lithium hydroxide, monohydrate → HCID 57635488, compound

HRID 535960Notes

Reaction equation

HRID 535960 reaction equation
[C:1]1([C:7]2[N:11]3[CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][C:10]3=[C:9]([C:24]([O:26]CC)=[O:25])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>CO>[C:20]([O:19][C:17]([N:15]1[CH2:14][CH2:13][CH2:12][N:11]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][C:9]([C:24]([OH:26])=[O:25])=[C:10]2[CH2:16]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57635142HCID 57635142, compound

Product 1

HCID 57635488HCID 57635488, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of Intermediate 39A (0.81 g, 2.10 mmol) and lithium hydroxide monohydrate (706 mg, 16.8 mmol) in methanol (20 mL) was heated at 65° C. for 5 hours. After evaporation of methanol, the residue was dissolved in brine. Concentrated HCl (2.5 mL) was added carefully to acidify and the mixture was extracted twice with DCM. The combined organic extracts were dried and evaporated to give Intermediate 39B as white solid (0.71 g 95% yield). LCMS (+ESI) m/z 357.9 [M+H]+.

Workup

  1. customAfter evaporation of methanol
  2. dissolutionthe residue was dissolved in brine
  3. additionConcentrated HCl (2.5 mL) was added carefully
  4. extractionthe mixture was extracted twice with DCM
  5. customThe combined organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-c57e15ac56fa40e0b63544c11e826471
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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