Lithium hydroxide, monohydrate → HCID 57635488, compound

HRID 2110226Notes

Reaction equation

HRID 2110226 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-a0d5b046a7804d5ab214a6d24b863e00
Source dataset
uspto-grants-2009_04
Patent number
US07517874B2

Reaction notes

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