Hydrochloric Acid → 3'-[(2-{[2-(3-Chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino][1,1'-biphenyl]-3-carboxylic acid--hydrogen chloride (1/1)

HRID 1266244Notes

Reaction equation

HRID 1266244 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@@H:9]([OH:31])[CH2:10][NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([O:29]C)=[O:28])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl>O.CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([C@@H:9]([OH:31])[CH2:10][NH:11][CH2:12][CH2:13][NH:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:29])=[O:28])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69713201HCID 69713201, compound

Product 1

HCID 102974433'-[(2-{[2-(3-Chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino][1,1'-biphenyl]-3-carboxylic acid--hydrogen chloride (1/1)Yield 165%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of methyl 3′-[(2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}ethyl)amino][1,1′-biphenyl]-3-carboxylate hydrochloride (10 g) and methanol (67 ml) at 40-50° C. is treated with 1.5N aqueous sodium hydroxide (60 ml) and held at this temperature for at least 1 hour. This solution is added to a solution of concentrated hydrochloric acid (10 ml) in water (20 ml) and methanol (33 ml) at 50° C. The resulting suspension is cooled to room temperature and filtered to give the title compound (8 g).

Workup

  1. waitheld at this temperature for at least 1 hour
  2. filtrationfiltered

Sources & evidence

ORD record
ord-0408d28d66c04527a3f94c8e3b085ced
Source dataset
uspto-grants-2003_04
Patent number
US06548523B2

Reaction notes

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