Ferulic Acid → Sitagliptin Ferulate

HRID 711121Notes

Reaction equation

HRID 711121 reaction equation
[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[C:29]([OH:42])(=[O:41])/[CH:30]=[CH:31]/[C:32]1[CH:40]=[CH:39][C:37]([OH:38])=[C:34]([O:35][CH3:36])[CH:33]=1>C(OCC)(=O)C>[CH:1]1[C:2]([CH2:10][C@@H:11]([NH2:28])[CH2:12][C:13]([N:15]2[CH2:27][C:19]3=[N:20][N:21]=[C:22]([C:23]([F:26])([F:25])[F:24])[N:18]3[CH2:17][CH2:16]2)=[O:14])=[C:3]([F:9])[CH:4]=[C:5]([F:8])[C:6]=1[F:7].[C:29]([O-:42])(=[O:41])/[CH:30]=[CH:31]/[C:32]1[CH:40]=[CH:39][C:37]([OH:38])=[C:34]([O:35][CH3:36])[CH:33]=1

Participants

4

Reactant 2

HCID 445858Ferulic AcidHCID 4369359Sitagliptin

Product 1

HCID 178490572Sitagliptin Ferulate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sitagliptin free base (4.0 gms) and ferulic acid (1.90 gms) were dissolved in ethyl acetate (32 ml) at 60° C. to 65° C. and the resultant clear solution left for slow solvent evaporation at room temperature for 48 hours. Precipitated solids were filtered off and dried at 50° C. to 55° C. for 6 hours to obtain the title compound. Yield: 3.48 gms.

Workup

  1. customPrecipitated solids
  2. filtrationwere filtered off
  3. customdried at 50° C. to 55° C. for 6 hours

Sources & evidence

ORD record
ord-fad660d56b354869b5381b610495df64
Source dataset
uspto-grants-2015_11
Patent number
US09181256B2

Reaction notes

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