Hydrochloric Acid → Solabegron

HRID 1069102Notes

Reaction equation

HRID 1069102 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][CH2:19][NH:20][CH2:21][C@@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[OH:23])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].O.[OH-].[Li+].Cl>CO.O>[Cl:30][C:26]1[CH:25]=[C:24]([C@@H:22]([OH:23])[CH2:21][NH:20][CH2:19][CH2:18][NH:17][C:13]2[CH:12]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=3)[CH:16]=[CH:15][CH:14]=2)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 9845280HCID 9845280, compound

Product 1

HCID 9887812SolabegronYield 55.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the (R)-3′-[[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]amino]-[1,1′-biphenyl]-3-carboxylic acid methyl ester (4.12 g) in methanol (60 mL) was added a solution of lithium hydroxide monohydrate (2.08 g) in water (20 mL). The mixture was stirred for 16 h, and 1 N hydrochloric acid was added until the mixture was neutral. The mixture was decanted and the residue was purified by flash silica chromatography eluting with 6:2:0.1 chloroform/methanol/ammonium hydroxide to afford a viscous oil. Trituration with ether and washing with water afforded the title compound as a white solid (2.22 g).

Workup

  1. customThe mixture was decanted
  2. customthe residue was purified by flash silica chromatography
  3. washeluting with 6:2:0.1 chloroform/methanol/ammonium hydroxide
  4. customto afford a viscous oil
  5. washTrituration with ether and washing with water

Sources & evidence

ORD record
ord-a97800fac98844ef9398d245ffbb37b1
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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