Lithium Hydroxide → HCID 135952366, compound

HRID 1916271Notes

Reaction equation

HRID 1916271 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:22](=[O:24])[NH:21][C:20]([CH3:25])=[N:19][C:18]=3[N:17]=[C:16]([S:26][CH2:27][C:28]3[N:29]=[C:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[S:31][CH:32]=3)[C:15]=2[C:40]#[N:41])=[CH:10][CH:9]=1)(=O)C.O1CCOCC1.[OH-].[Li+]>O>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C:30]2[S:31][CH:32]=[C:28]([CH2:27][S:26][C:16]3[C:15]([C:40]#[N:41])=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][OH:4])=[CH:9][CH:10]=4)[C:23]4[C:22](=[O:24])[NH:21][C:20]([CH3:25])=[N:19][C:18]=4[N:17]=3)[N:29]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 3939Lithium Hydroxide2×HCID 312751,4-DioxaneHCID 136052979HCID 136052979, compound

Product 1

HCID 135952366HCID 135952366, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

24 mg (0.04 mmol) of the compound from Example 8A were initially charged in 2.3 ml of a 2:1 mixture of dioxane and water, and 1.9 mg (0.08 mmol) of lithium hydroxide were added. The reaction mixture was stirred at RT for 4 h. A further 1.9 mg (0.08 mmol) of lithium hydroxide were added, and the mixture was stirred for another 4 h. 2 ml of water were added to the reaction. The mixture was extracted three times in total with in each case 4 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate and the solvent was removed on a rotary evaporator. The residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for another 4 h
  3. extractionThe mixture was extracted three times in total with in each case 4 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customthe solvent was removed on a rotary evaporator
  6. customThe residue was purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-968499250f514d278575fb5ce0e07128
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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