Lithium Hydroxide → HCID 178526040, compound

HRID 1045104Notes

Reaction equation

HRID 1045104 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][S:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([Cl:33])[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:21]=3)=[CH:17][C:11]=2[N:10]=1)(C)(C)C.[Li+].[OH-]>CO.O>[Cl:33][C:15]1[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[CH:17][C:11]2[N:10]=[C:9]([S:8][CH2:7][C:6]([OH:34])=[O:5])[NH:13][C:12]=2[CH:14]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178451391HCID 178451391, compound

Product 1

HCID 178526040HCID 178526040, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of compound 33-1 (29.0 mg, 0.059 mmol) in MeOH (6 mL) was added to 5% aqueous LiOH (3 mL) and the mixture was stirred at rt for 20 h. The mixture was then diluted with water (2 mL), evaporated to ½ of the initial volume and acidified with 5% aqueous HCl. The solution was extracted with EtOAc (3 mL then 1 mL, twice). The organic layers were combined, washed with water (three times, 1 mL) and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1.0 mL), filtered and purified by reverse-phase HPLC to give the title compound as off-white solid. LR-MS (API-ES): calculated for C23H15ClN2O3S 434.1, observed m/e 435.0 (M+H)+ (Rt 2.96 min).

Workup

  1. customevaporated
  2. extractionThe solution was extracted with EtOAc (3 mL
  3. washwashed with water (three times, 1 mL)
  4. customevaporated to dryness in vacuo
  5. dissolutionThe resulting oily residue was dissolved in DMSO (1.0 mL)
  6. filtrationfiltered
  7. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-a8774d3355f24efb8fa78758ba170ad9
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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