Methanesulfonic Acid → HCID 12049889, compound

HRID 2185028Notes

Reaction equation

HRID 2185028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][NH:15][C@@H:16]([CH3:26])[C@H:17]([OH:25])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[O:5][CH2:6][C:7]([OH:9])=[O:8].CS(O)(=O)=O>C(O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][NH:15][C@@H:16]([CH3:26])[C@H:17]([OH:25])[C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[O:5][CH2:6][C:7]([O:9][CH2:13][C:12]1[CH:11]=[CH:10][CH:4]=[CH:3][CH:2]=1)=[O:8]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 11660892HCID 11660892, compound

Product 1

HCID 12049889HCID 12049889, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Procedure

A solution of 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenoxy]acetic acid (200 mg) and methanesulfonic acid (38 μl) in benzyl alcohol (1.0 ml) was stirred for 2 days at room temperature. Purification of the reaction mixture by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=20/1) gave benzyl 2-[3-chloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-phenoxy]acetate (136 mg).

Workup

  1. customPurification of the reaction mixture by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=20/1)

Sources & evidence

ORD record
ord-e2c92167074e4aa8a4b5ac1f8f409590
Source dataset
uspto-grants-2002_06
Patent number
US06399660B1

Reaction notes

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