Fumaric Acid → HCID 67366201, compound

HRID 452018Notes

Reaction equation

HRID 452018 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:36])[NH:24][C@@H:25]([CH2:29][C@H:30]3[CH2:35][CH2:34][CH2:33][O:32][CH2:31]3)[CH2:26][NH:27][CH3:28])[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C(O)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:36])[NH:24][C@@H:25]([CH2:29][C@H:30]3[CH2:35][CH2:34][CH2:33][O:32][CH2:31]3)[CH2:26][NH:27][CH3:28])[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 58017399HCID 58017399, compound

Product 1

HCID 67366201HCID 67366201, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution of methyl 2-((R)-(3-fluorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate (71.2 mg, 0.14 mmol) was treated with fumaric acid (16.3 mg, 0.14 mmol). The solvent was removed in vacuo and the residue re-dissolved in water. The solution was frozen using a dry ice-acetone bath and placed on a lypholizer to afford methyl 2-((R)-(3-fluorophenyl)((R)-1-((S)-1-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate fumaric acid salt (87.46 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue re-dissolved in water
  3. temperatureThe solution was frozen

Sources & evidence

ORD record
ord-bcb375fccc024763b35bcb0622dd2755
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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