Hydrochloric Acid → 6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-hydroxy-4-oxobutoxy]phenyl]benzo[b]thiophene

HRID 1595044Notes

Reaction equation

HRID 1595044 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]C)=[O:36])=[CH:27][CH:26]=3)[S:7][C:6]=2[CH:39]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[CH:29][CH:30]=3)[S:7][C:6]=2[CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 217063196-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-methoxy-4-oxobutoxy]phenyl]benzo[b]thiophene

Product 1

HCID 217063136-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-hydroxy-4-oxobutoxy]phenyl]benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

6-Hydroxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-[4-methoxy-4-oxobutoxy]phenyl]benzo[b]thiophene (147 mg) was dissolved in THF:MeOH:H2O (3:1:1, 3.0 mL), treated with lithium hydroxide monhydrate (12 mg) in one portion, and allowed to stir at ambient temperature for 4 days. The reaction mixture was neutralized with dilute HCl and concentrated in vacuo. The residue was dissolved in methanol. The solution was transfered to a clean vial and solvent was removed with a stream of nitrogen to give the product as an off-white solid. (100 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol
  3. customwas removed with a stream of nitrogen

Sources & evidence

ORD record
ord-72f3665d7aaf4373bb6acb81a9f19814
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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