Hydrochloric Acid → ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-2-methylpropionate hydrochloride

HRID 1006460Notes

Reaction equation

HRID 1006460 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[CH2:17][CH2:18][NH:19][C@@H:20]([CH3:30])[C@H:21]([OH:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[O:5][C:6]([CH3:13])([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl>C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[CH2:17][CH2:18][NH:19][C@@H:20]([CH3:30])[C@H:21]([OH:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[O:5][C:6]([CH3:13])([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12096594ethyl 2-[3-Chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]-2-methylpropionate

Product 1

HCID 69883633ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]-2-methylpropionate hydrochlorideYield 190%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]-amino]ethyl]phenoxy]-2-methylpropionate (170 mg) in ethyl acetate (7.8 ml) was added 4N hydrogen chloride in ethyl acetate solution (200 μl) at room temperature. After the solvent was removed under reduced pressure, diethyl ether was added to the residue, and collection of the insoluble material by filtration gave ethyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]-2-methyl-propionate hydrochloride (175 mg).

Workup

  1. customAfter the solvent was removed under reduced pressure, diethyl ether
  2. additionwas added to the residue, and collection of the insoluble material by filtration

Sources & evidence

ORD record
ord-4bf7b79e44554bee80b46c98b91f7f9f
Source dataset
uspto-grants-2004_09
Patent number
US06790865B2

Reaction notes

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