Oxalic Acid → Oxalate

HRID 572864Notes

Reaction equation

HRID 572864 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-2ba09eb5d2294c80a4953c7ff87b437f
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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