Oxalic Acid → Oxalate

HRID 2404454Notes

Reaction equation

HRID 2404454 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([C:28]2[S:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[O:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O.[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47]>ClCCl.CC(C)=O>[S:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=[C:28]1[CH:19]([O:20][CH:21]1[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]1)[C:15]1[CH:14]=[C:13]([S:12][CH2:11][CH2:10][CH2:9][CH2:8][NH2:7])[CH:18]=[CH:17][CH:16]=1.[C:45]([O-:50])(=[O:49])[C:46]([O-:48])=[O:47]

Participants

7

Reactant 3

HCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 67511992HCID 67511992, compound

Product 2

HCID 71081OxalateHCID 66835969HCID 66835969, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

(4-{3-[Benzothiazol-2-yl-(1-methyl-piperidin-4-yloxy)-methyl]-phenylsulfanyl}-butyl)-carbamic acid tert-butyl ester (140 mg) is dissolved in dichloromethane (1 mL) and trifluoroacetic acid (0.4 mL) is added. The reaction mixture is stirred at room temperature for 1 hour. The mixture is evaporated to dryness. The residue is basified by adding a solution of saturated sodium carbonate to pH 10 and the aqueous phase is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/1). The residue is added to oxalic acid (1 equivalent) in acetone (0.5 ml), and the precipitate is filtered and dry to give 4-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)-methyl]phenylsulfanyl}butylamine, oxalate melting at 108° C.

Workup

  1. customThe mixture is evaporated to dryness
  2. additionby adding a solution of saturated sodium carbonate to pH 10
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/1)
  7. filtrationthe precipitate is filtered
  8. customdry

Sources & evidence

ORD record
ord-ba5308e34b6e4686a3bc92f91db92295
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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