Lithium Hydroxide → HCID 10162022, compound

HRID 857360Notes

Reaction equation

HRID 857360 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]1[C:9]2=[C:10]([S:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:11]3[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6]1.[Li+].[OH-]>C1COCC1.CO.CC(O)=O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([S:23][C:10]2[C:11]3[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[N:8]3[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:31])=[O:2])[C:9]=23)=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 91428377HCID 91428377, compound

Product 1

HCID 10162022HCID 10162022, compoundYield 89.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step 7 (23 mg, 0.048 mmol) in THF (3 mL) and MeOH (1 mL) at RT was added 1M LiOH (0.24 mL, 0.24 mmol). After stirring at r.t. for 4.5 hours, HOAc (10 drops) was added and the solvent was evaporated. The residue was taken up in EtOAc/H2O and the organic phase was washed with brine, dried (MgSO4), and filtered. Upon removal of the solvent, the resulting solid was stirred with 1:5 EtOAc:hexane to give a beige solid (20 mg).

Workup

  1. customthe solvent was evaporated
  2. washthe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customUpon removal of the solvent
  6. stirringthe resulting solid was stirred with 1:5 EtOAc

Sources & evidence

ORD record
ord-5c9a9d8c59054ab596560753a67560ea
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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