Oxalic Acid → HCID 86647028, compound

HRID 870329Notes

Reaction equation

HRID 870329 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(O)(C)C.[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35]>O>[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:33]([O-:38])(=[O:37])[C:34]([O-:36])=[O:35]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 3776IsopropanolHCID 4369359Sitagliptin

Product 1

HCID 86647028HCID 86647028, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 30 minutes to obtain a clear dissolution. Oxalic acid (1.54 g) dissolved in water (5 mL) is added and the reaction mixture is refluxed for about 1 hour. The reaction mixture is cooled to about 30° C. and stirred for about 22 hours. The separated solid is filtered, washed with isopropanol (5 mL), and dried under reduced pressure at about 40° C. for about 2.5 hours to afford the title compound. (Yield: 5.8 g; MC: 6.54% w/w; HPLC purity: 99.95%)

Workup

  1. customto obtain
  2. dissolutiona clear dissolution
  3. additionis added
  4. temperaturethe reaction mixture is refluxed for about 1 hour
  5. temperatureThe reaction mixture is cooled to about 30° C.
  6. filtrationThe separated solid is filtered
  7. washwashed with isopropanol (5 mL)
  8. customdried under reduced pressure at about 40° C. for about 2.5 hours

Sources & evidence

ORD record
ord-3acafde0a80a4ca4a0c866d82bbe1f75
Source dataset
uspto-grants-2015_03
Patent number
US08969558B2

Reaction notes

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