Diisopropyl Ether → Sitagliptin Ferulate

HRID 711123Notes

Reaction equation

HRID 711123 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(OC(C)C)(C)C>CO>[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

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 445858Ferulic AcidHCID 4369359Sitagliptin

Product 1

HCID 178490572Sitagliptin Ferulate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sitagliptin free base (2.0 gms) and ferulic acid (0.95 gms) were dissolved in methanol (12 ml) at 60° C. to 65° C. and the resultant solution was cooled to room temperature. Isopropyl ether (120 ml) was added to the clear solution and stirred for 12 hours. Filtered the precipitated solids and dried at 70° C. to 75° C. for 12 hours to obtain the title compound.

Workup

  1. filtrationFiltered the precipitated solids
  2. customdried at 70° C. to 75° C. for 12 hours

Sources & evidence

ORD record
ord-373c22d4c44c40688e50febeea3ff640
Source dataset
uspto-grants-2015_11
Patent number
US09181256B2

Reaction notes

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