p-Toluenesulfonate → Methyl p-toluenesulfonate

HRID 249701Notes

Reaction equation

[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[CH3:12][C@H]1CN(C2C=CC(OC(F)(F)F)=CC=2)C[C@@H](C)N1S(C1C=CC=C2C=1C[C@@H](C(O)=O)C2)(=O)=O.[S:46]([C:50]1[CH:56]=[CH:55][C:53]([CH3:54])=[CH:52][CH:51]=1)([O-:49])(=[O:48])=[O:47]>>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].[CH3:12][O:47][S:46]([C:50]1[CH:56]=[CH:55][C:53]([CH3:54])=[CH:52][CH:51]=1)(=[O:49])=[O:48]

Participants

Reactant 2

HCID 85570p-Toluenesulfonate8×

HCID 16048651KD-3010

Product 2

HCID 6645Methyl p-toluenesulfonate

HCID 85570p-Toluenesulfonate

Procedure

The methyl ester precursor of (S)-4-[cis-2,6-dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carboxylic acid tosylate (hereinafter optionally referred to as “Compound 1 tosylate”) was used for this experiment instead of Compound 1 tosylate due to the unsuitability of the Compound 1 tosylate crystals for X-ray structure determination. Compound 1 tosylate methyl ester was prepared via an esterification of Compound 1 tosylate followed by recrystallization from isopropanol. Other experiments have established that the stereochemistry is retained in converting the methyl ester to Compound 1 tosylate.

Workup

customfollowed by recrystallization from isopropanol

Sources & evidence

ORD record: ord-a67dd3abc5b34ca3b4a0be879f6a7f7a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863276B2

Reaction notes

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