Ferulic Acid → Sitagliptin Ferulate

HRID 1050896Notes

Reaction equation

HRID 1050896 reaction equation
[C:1]([OH:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1.[CH:15]1[C:16]([CH2:24][C@@H:25]([NH2:42])[CH2:26][C:27]([N:29]2[CH2:41][C:33]3=[N:34][N:35]=[C:36]([C:37]([F:40])([F:39])[F:38])[N:32]3[CH2:31][CH2:30]2)=[O:28])=[C:17]([F:23])[CH:18]=[C:19]([F:22])[C:20]=1[F:21]>C(O)C>[CH:15]1[C:16]([CH2:24][C@@H:25]([NH2:42])[CH2:26][C:27]([N:29]2[CH2:41][C:33]3=[N:34][N:35]=[C:36]([C:37]([F:40])([F:39])[F:38])[N:32]3[CH2:31][CH2:30]2)=[O:28])=[C:17]([F:23])[CH:18]=[C:19]([F:22])[C:20]=1[F:21].[C:1]([O-:14])(=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6]([O:7][CH3:8])[CH:5]=1

Participants

4

Reactant 2

HCID 445858Ferulic AcidHCID 4369359Sitagliptin

Product 1

HCID 178490572Sitagliptin Ferulate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ferulic acid (2.0 gms) was dissolved in ethanol (10 ml) and sitagliptin free base (1.9 gms) was added to the clear solution and stirred for 15 min. Additional ethanol (10 ml) was added to the semi precipitated reaction mass and stirring was continued for 48 hours at room temperature. Precipitated solids were filtered off and dried at 70° C. to 75° C. for 24 hours to obtain the title compound. Yield: 1.37 gms.

Workup

  1. customprecipitated
  2. customreaction mass
  3. stirringstirring
  4. waitwas continued for 48 hours at room temperature
  5. customPrecipitated solids
  6. filtrationwere filtered off
  7. customdried at 70° C. to 75° C. for 24 hours

Sources & evidence

ORD record
ord-bcc7209b8a0f44f6a18ed50c70483d5a
Source dataset
uspto-grants-2016_07
Patent number
US09388113B2

Reaction notes

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