Lithium hydroxide, monohydrate → HCID 117599121, compound

HRID 522420Notes

Reaction equation

HRID 522420 reaction equation
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:10]([NH:12][C@@H:13]([CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:14]([O:16]C)=[O:15])=[O:11])[CH2:2][CH2:3][C:4]#[CH:5].O.[OH-].[Li+].OS([O-])(=O)=O.[K+]>C1COCC1.CO>[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:10]([NH:12][C@@H:13]([CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:14]([OH:16])=[O:15])=[O:11])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516920Potassium bisulfateHCID 89590889HCID 89590889, compound

Product 1

HCID 117599121HCID 117599121, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product from Step 1 (1.88 g, 5.81 mmol) in THF (20 ml) and MeOH (10 mL) was added an aq. 2M solution of lithium hydroxide monohydrate (14.53 ml, 29.1 mmol). The reaction was stirred at 50° C. for 20 hours at which stage TLC indicated no more starting material. The reaction was treated with 10% aq. KHSO4 and extracted with EtOAc. The organic fractions were washed with brine, dried over sodium sulfate, evaporated and dried to provide the desired compound, which was used for the next step without purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic fractions were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customdried

Sources & evidence

ORD record
ord-a8c3bb10b4fa447c9c949bdb59409313
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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