Lactic Acid → HCID 86645865, compound

HRID 1876797Notes

Reaction equation

HRID 1876797 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:34])(=[O:33])[CH:30]([CH3:32])[OH:31]>C(O)(C)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-:34])(=[O:33])[CH:30]([CH3:32])[OH:31]

Participants

4

Reactant 2

HCID 612Lactic AcidHCID 4369359Sitagliptin

Product 1

HCID 86645865HCID 86645865, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Sitagliptin (5 g) and isopropanol (75 mL) are charged into a round-bottom flask and the mixture is heated to about 80° C. for about 20 minutes to obtain a clear dissolution. Lactic acid (1.10 g) is added and the reaction mixture is refluxed for about 1.5 hours. The reaction mixture is cooled to about 30° C. and stirred for about 8.5 hours. The separated solid is filtered, washed with isopropanol (5 mL), and dried under reduced pressure at about 45° C. for about 2 hours to afford the title compound. (Yield: 4.0 g; MC: 0.62% w/w; HPLC purity: 99.75%)

Workup

  1. customto obtain
  2. dissolutiona clear dissolution
  3. temperaturethe reaction mixture is refluxed for about 1.5 hours
  4. temperatureThe reaction mixture is cooled to about 30° C.
  5. filtrationThe separated solid is filtered
  6. washwashed with isopropanol (5 mL)
  7. customdried under reduced pressure at about 45° C. for about 2 hours

Sources & evidence

ORD record
ord-14c4e100bdbf4fe0aaa2feea8e33d755
Source dataset
uspto-grants-2012_11
Patent number
US08309724B2

Reaction notes

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