Isopropanol → HCID 86647026, compound

HRID 870327Notes

Reaction equation

HRID 870327 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].[CH:29]([OH:32])([CH3:31])C>C(O)(=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-:32])(=[O:14])[CH3:31]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 4369359Sitagliptin

Product 1

HCID 86647026HCID 86647026, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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. Acetic acid (0.73 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 30° C. for about 3.5 hours to afford the title compound. (Yield: 5.6 g; MC: 0.79% w/w; HPLC purity: 99.81%)

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 30° C. for about 3.5 hours

Sources & evidence

ORD record
ord-f730ce0ab50e4745844e339a49fda365
Source dataset
uspto-grants-2015_03
Patent number
US08969558B2

Reaction notes

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