2-Dimethylaminopyridine → HCID 86745470, compound

HRID 1534333Notes

Reaction equation

HRID 1534333 reaction equation
CN(C1C=CC=CN=1)C.[O:10]=[N:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14].S(Cl)(C)(=O)=O.Cl.[CH3:25][O:26][C:27](=[O:34])[C@H:28]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH2:29]>O1CCCC1.ClCCl.C(N(CC)CC)C>[CH3:25][O:26][C:27](=[O:34])[C@H:28]([CH2:30][CH:31]([CH3:33])[CH3:32])[NH:29][C:16](=[O:18])[C@H:12]([CH:13]([CH3:15])[CH3:14])[N:11]=[O:10]

Participants

8

Reactant 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 2723695Leucine methyl ester hydrochlorideHCID 71650555HCID 71650555, compound

Product 1

HCID 86745470HCID 86745470, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

15.1 g of dimethylaminopyridine were added to a solution of 13.0 g of the ketovaline obtained in step a) in 100 ml of tetrahydrofuran. While stirring, 22.7 g of triethylamine were added dropwise, and the reaction mixture was cooled to -20° C. Subsequently a solution of 14.1 g of mesyl chloride in 50 ml of tetrahydrofuran was added dropwise, and the mixture was stirred for a further 20 minutes. Then a solution of 20.4 g of leucine methyl ester hydrochloride in 150 ml of dichloromethane was added dropwise, and the mixture was again stirred for 20 minutes. The mixture was then allowed to warm slowly to room temperature, undissolved constituents were separated by filtration, and the solvent was removed from the filtrate under reduced pressure. The residue was taken up in distilled water and extracted with dichloromethane. The collected organic phases were then dried over sodium sulfate and, after filtration, the solvent was removed under reduced pressure. 14.7 g of the title compound remained as a yellow oil.

Workup

  1. stirringthe mixture was stirred for a further 20 minutes
  2. stirringthe mixture was again stirred for 20 minutes
  3. temperatureto warm slowly to room temperature
  4. customundissolved constituents were separated by filtration
  5. customthe solvent was removed from the filtrate under reduced pressure
  6. extractionextracted with dichloromethane
  7. dry with materialThe collected organic phases were then dried over sodium sulfate
  8. filtrationafter filtration
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c69f252359bf4dbaacb364c4cc775e0b
Source dataset
uspto-grants-1992_02
Patent number
US05089492

Reaction notes

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