2-Chloromandelic acid → HCID 131732760, compound

HRID 1473011Notes

Reaction equation

HRID 1473011 reaction equation
[CH3:1][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:5])[CH3:3].[Cl:31][C:32]1[CH:42]=[CH:41][CH:40]=[CH:39][C:33]=1[CH:34]([OH:38])[C:35]([OH:37])=[O:36]>C(OCC)(=O)C>[CH3:3][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:18])[CH3:19])=[O:5])[CH3:1].[Cl:31][C:32]1[CH:42]=[CH:41][CH:40]=[CH:39][C:33]=1[CH:34]([OH:38])[C:35]([O-:37])=[O:36]

Participants

4

Reactant 2

HCID 977202-Chloromandelic acidHCID 6918558Fesoterodine

Product 1

HCID 131732760HCID 131732760, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Fesoterodine base (5 g) and ethyl acetate (20 ml) were added to a four-neck two liter round bottom flask. Further, 2-chloro-mandelic acid (2.3 g) was added at 25° C. to 35° C. The reaction mass was stirred for 2 hours at 25° C. to 35° C. The reaction mass was cooled to 0° C. to 5° C. The product was filtered and washed with chilled ethyl acetate (2×2.5 ml). The wet cake was dried at 60° C. to 65° C. for 8 to 10 to afford solid fesoterodine 2-chloro-mandelate (Purity by HPLC: 99.8%).

Workup

  1. temperatureThe reaction mass was cooled to 0° C. to 5° C
  2. filtrationThe product was filtered
  3. washwashed with chilled ethyl acetate (2×2.5 ml)
  4. customThe wet cake was dried at 60° C. to 65° C. for 8 to 10

Sources & evidence

ORD record
ord-6f4b90c77b974d53ae6b71c68e2c6c12
Source dataset
uspto-grants-2015_04
Patent number
US09012678B2

Reaction notes

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