Ethyl Acetate → Sitagliptin

HRID 1876785Notes

Reaction equation

HRID 1876785 reaction equation
[OH-].[Na+].C(OC(=O)C)C.[CH:9]1[C:10]([CH2:18][C@@H:19]([NH2:36])[CH2:20][C:21]([N:23]2[CH2:35][C:27]3=[N:28][N:29]=[C:30]([C:31]([F:34])([F:33])[F:32])[N:26]3[CH2:25][CH2:24]2)=[O:22])=[C:11]([F:17])[CH:12]=[C:13]([F:16])[C:14]=1[F:15].C1(C)C=CC([C@@](C([O-])=O)(O)[C@@](C2C=CC(C)=CC=2)(O)C([O-])=O)=CC=1>O>[CH:9]1[C:10]([CH2:18][C@@H:19]([NH2:36])[CH2:20][C:21]([N:23]2[CH2:35][C:27]3=[N:28][N:29]=[C:30]([C:31]([F:34])([F:33])[F:32])[N:26]3[CH2:25][CH2:24]2)=[O:22])=[C:11]([F:17])[CH:12]=[C:13]([F:16])[C:14]=1[F:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 131730057HCID 131730057, compound

Product 1

HCID 4369359SitagliptinYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

10% sodium hydroxide solution (1 mL) is added to a mixture of ethylacetate (10 mL), water (5 mL), sitagliptin di-p-tolyl-L-tartarate (0.4 g) under stirring at about 5° C. The mixture is stirred for about 30 minutes. The layers are separated and the aqueous layer is extracted with ethyl acetate (10 mL). The combined organic layer is distilled off completely to afford 0.2 gm of sitagliptin freebase.

Workup

  1. stirringThe mixture is stirred for about 30 minutes
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (10 mL)
  4. distillationThe combined organic layer is distilled off completely

Sources & evidence

ORD record
ord-326e641063d040bcb2baebb0b9971068
Source dataset
uspto-grants-2012_11
Patent number
US08309724B2

Reaction notes

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