Lithium Hydroxide → HCID 19974933, compound

HRID 1451522Notes

Reaction equation

HRID 1451522 reaction equation
[CH2:1]([CH:8]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=2)[C:15]=1[CH3:33])[C:9]([O:11]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[CH2:1]([CH:8]([CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([Br:32])=[CH:30][CH:31]=2)[C:15]=1[CH3:33])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19974931HCID 19974931, compound

Product 1

HCID 19974933HCID 19974933, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of the methyl ester from Step 2 (40 mg, 0.08 mmol) in 3 mL THF and 5 mL MeOH was added 1 mL of 1M LiOH. The resulting solution was stirred 30 h at room temperature, then quenched with aqueous NH4Cl and concentrated in vacuo. The residue was partitioned between 1M HCl and EtOAc, washed with brine, dried over Na2SO4 and evaporated to give 30 mg of the title compound.

Workup

  1. customquenched with aqueous NH4Cl
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 1M HCl and EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-c3bdbcdc33e04a9c95c0d0d277cb0aca
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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