Ferulic Acid → Sitagliptin Ferulate

HRID 711122Notes

Reaction equation

HRID 711122 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-1c98c64d18394714b1c7484e483a1f37
Source dataset
uspto-grants-2015_11
Patent number
US09181256B2

Reaction notes

Loading…