Hydrochloric Acid → HCID 15895332, compound

HRID 1862632Notes

Reaction equation

HRID 1862632 reaction equation
CN(C)[C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH:14][C@@H:15]([CH3:25])[C@H:16]([OH:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:8][C:7]=1[N:26]([CH3:28])[CH3:27].Cl.[OH-:32].[Na+]>>[CH3:28][N:26]([CH3:27])[C:7]1[CH:8]=[C:9]([CH2:12][CH2:13][NH:14][C@@H:15]([CH3:25])[C@H:16]([OH:24])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:29])=[O:32]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15895334HCID 15895334, compound

Product 1

HCID 15895332HCID 15895332, compound

Procedure

N,N-Dimethyl-2-[2-dimethylamino-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetamide (503 mg) was dissolved in 1N aqueous sodium hydroxide solution (6.0 ml), and the solution was stirred for 20 hours at room temperature. 1N Hydrochloric acid (6.0 ml) was added to the stirred reaction mixture under ice-cooling, and direct purification of the resulting mixture by medium pressure liquid column chromatography on ion exchange resin (Nippon Rensui Co. Ltd., DIAION® HP-20) (eluent:water/methanol=1/0 to 1/1) gave 2-[2-dimethylamino-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid (330 mg).

Workup

  1. temperaturecooling
  2. customdirect purification of the resulting mixture by medium pressure liquid column chromatography on ion exchange resin (Nippon Rensui Co. Ltd., DIAION® HP-20) (eluent:water/methanol=1/0 to 1/1)

Sources & evidence

ORD record
ord-5ba9e5ce58874bfe925f57f51d501298
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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