HCID 12049888, compound → ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]acetate hydrochloride

HRID 2185027Notes

Reaction equation

HRID 2185027 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][NH:17][C@@H:18]([CH3:28])[C@H:19]([OH:27])[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(OC(=O)C)C.Cl>C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][NH:17][C@@H:18]([CH3:28])[C@H:19]([OH:27])[C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 12049888HCID 12049888, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 69828654ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]acetate hydrochlorideYield 168.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-acetate (120 mg) in ethyl acetate (2.0 ml) was added 4N hydrogen chloride ethyl acetate solution (220 μl) under ice-cooling, and the mixture was vigorously stirred for an hour at room temperature. Collection of the resulting precipitates by filtration gave ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]acetate hydrochloride (110 mg).

Workup

  1. temperaturecooling
  2. customCollection of the resulting
  3. customprecipitates by filtration

Sources & evidence

ORD record
ord-c6734646b2504ef8a03c878fa6fa0c13
Source dataset
uspto-grants-2002_06
Patent number
US06399660B1

Reaction notes

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