Sodium Hydroxide → HCID 69818210, compound

HRID 2417446Notes

Reaction equation

HRID 2417446 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@@H:9]([OH:35])[CH2:10][NH:11][C@H:12]([CH2:33][OH:34])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+:37]>CO>[Cl:2][C:3]1[CH:4]=[C:5]([C@@H:9]([OH:35])[CH2:10][NH:11][C@H:12]([CH2:33][OH:34])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([C:27]([O-:29])=[O:28])=[CH:31][CH:32]=3)=[O:22])=[CH:18][CH:19]=2)[CH:6]=[CH:7][CH:8]=1.[Na+:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69817794HCID 69817794, compound

Product 1

HCID 69818210HCID 69818210, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 4-[[[4-[(2S)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-hydroxypropyl]-phenyl]amino]carbonyl]benzoate hydrochloride (101 mg) in methanol (4.0 ml) was added 1N sodium hydroxide solution (486 μl) and the mixture was refluxed for 90 minutes. After cooling to room temperature, the solvent was removed by evaporation. The residual solid was applied on a solid phase extraction cartridge (BOND ELUT C18, 20 ml, VARIAN) and eluted with water and methanol successively. The eluents containing the target compound were combined and concentrated in vacuo to give sodium 4-[[[4-[(2S)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-hydroxypropyl]-phenyl]amino]carbonyl]benzoate (66.7 mg) as an off-white solid.

Workup

  1. temperaturethe mixture was refluxed for 90 minutes
  2. customthe solvent was removed by evaporation
  3. extractionThe residual solid was applied on a solid phase extraction cartridge (BOND ELUT C18, 20 ml, VARIAN)
  4. washeluted with water and methanol successively
  5. additionThe eluents containing the target compound
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1dc06b7e4894675a1349c2c214d9e8a
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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