Potassium Sodium Tartrate → HCID 57504565, compound
Reaction equation
C[Al](C)C.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].[N:12]1([CH2:16][C@H:17]([OH:22])[C:18](OC)=[O:19])[CH2:15][CH2:14][CH2:13]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O>[N:12]1([CH2:16][C@H:17]([OH:22])[C:18]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=2)=[O:19])[CH2:15][CH2:14][CH2:13]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
Trimethylaluminium (8.31 mL, 16.62 mmol) was added to pyridin-2-amine (1.360 g, 14.45 mmol) in toluene (30 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes. (S)-Methyl 3-(azetidin-1-yl)-2-hydroxypropanoate (Intermediate BC2) (2.3 g, 14.45 mmol) in toluene (10 mL) and THF (5 mL) was added and the resulting solution was allowed to warm to room temperature and then heated at 60° C. for 8 hours. The reaction cooled and 20% Rochelle salt (50 mL) added followed by EtOAc (50 mL) and the mixture stirred at ambient temperature overnight. The organic phase separated and the aqueous phase re-extracted with EtOAc (2×50 mL). The organic phases were combined, dried (MgSO4) and evaporated to afford the product (2.7 g) which was used without further purification.
Workup
- temperatureto warm to room temperature
- temperatureheated at 60° C. for 8 hours
- temperatureThe reaction cooled
- stirringthe mixture stirred at ambient temperature overnight
- customThe organic phase separated
- extractionthe aqueous phase re-extracted with EtOAc (2×50 mL)
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-5e368e1fee17422b9fa49f1eb0427cac
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143263B2
Reaction notes
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