Hydrochloric Acid → 4'-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylic acid hydrochloride

HRID 2220437Notes

Reaction equation

HRID 2220437 reaction equation
[OH:1][C@H:2]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23]C)=[O:22])=[C:17]([S:25][CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[CH:11][CH:10]=1)[CH3:4].[OH-].[Na+].[ClH:38]>CO>[ClH:38].[OH:1][C@H:2]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[C:17]([S:25][CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[CH:13][CH:14]=1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69103361methyl 4'-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylate

Product 1

HCID 691028394'-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4′-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylate (110 mg) in methanol (1.65 ml) was added sodium hydroxide aqueous solution (1N 1.11 ml) and stirred at room temperature overnight. To the mixture was added hydrochloric acid aqueous solution (1N, 1.22 ml) and concentrated in vacuo. The residue was solved with methanol, added hydrogen chloride 1,4-dioxane solution (4M), concentrated in vacuo and dried to give 4′-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethoxy]-3-(isopropylthio)-4-biphenylcarboxylic acid hydrochloride (97 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. additionadded hydrogen chloride 1,4-dioxane solution (4M)
  3. concentrationconcentrated in vacuo
  4. customdried

Sources & evidence

ORD record
ord-706566f822f54639b63be178769e5a2d
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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