Potassium Sodium Tartrate → HCID 57504738, compound

HRID 1098275Notes

Reaction equation

HRID 1098275 reaction equation
C[Al](C)C.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11].[Si:12]([O:29][CH2:30][CH:31]1[CH2:34][N:33]([CH2:35][C@H:36]([OH:41])[C:37](OC)=[O:38])[CH2:32]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Si:12]([O:29][CH2:30][CH:31]1[CH2:34][N:33]([CH2:35][C@H:36]([OH:41])[C:37]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=2)=[O:38])[CH2:32]1)([C:25]([CH3:26])([CH3:28])[CH3:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 104392-AminopyridineHCID 16682925TrimethylaluminumHCID 66813352HCID 66813352, compound

Product 1

HCID 57504738HCID 57504738, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Trimethylaluminium (1.344 mL, 2.69 mmol) was added to pyridin-2-amine (220 mg, 2.34 mmol) in toluene (20 mL) cooled to 0° C. under nitrogen over a period of 10 minutes. The resulting solution was stirred at 0° C. for 10 minutes. (S)-Methyl 3-(3-((tert-butyldiphenylsilyloxy)methyl)azetidin-1-yl)-2-hydroxypropanoate (Intermediate BG2) (1.43 g, 2.34 mmol) in toluene (5 mL) was added over 10 minutes and the reaction was allowed to warm to room temperature and then heated at 110° C. for 2 hours. The reaction mixture was cooled and poured into a 20% solution of Rochelle salt (30 mL), diluted with ethyl acetate (80 mL) and stirred for 1 hour. The organic phase was separated, washed with water and brine, dried over MgSO4 filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% (10% MeOH in DCM) in DCM to afford the product (681 mg, 59.5%).

Workup

  1. temperatureto warm to room temperature
  2. temperatureheated at 110° C. for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. stirringstirred for 1 hour
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 100% (10% MeOH in DCM) in DCM

Sources & evidence

ORD record
ord-75c0aabba7634d3d9fd8edb4b5764b7f
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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