Potassium Carbonate → N-Boc-L-serine methyl ester

HRID 1972181Notes

Reaction equation

HRID 1972181 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:15][O:13][C:12](=[O:14])[C@H:9]([CH2:10][OH:11])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 7019177N-Boc-L-serine methyl esterYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice cooling, 18.7 g of N-Boc-L-serine was dissolved in 200 ml of DMF and 13.25 g of solid K2CO3 was added and suspended for 15 minutes, and then 41.6 g (3.2 eq) of Mel was added, followed by stirring for 24 hours. After the reaction, the reaction solution was filtered through celite and concentrated. The residue was extracted by liquid separation using 400 ml of water and 150 ml×4 of ethyl acetate and dried over sodium sulfate. The ethyl acetate layer was concentrated and subjected to silica gel column chromatography to obtain 17.1 g (87.4%) of an N-Boc-L-serine methyl ester as a transparent oily product.

Workup

  1. addition41.6 g (3.2 eq) of Mel was added
  2. customAfter the reaction
  3. filtrationthe reaction solution was filtered through celite
  4. concentrationconcentrated
  5. extractionThe residue was extracted by liquid separation
  6. dry with materialdried over sodium sulfate
  7. concentrationThe ethyl acetate layer was concentrated

Sources & evidence

ORD record
ord-998dfe75489e4c9ebd042248cebd28c5
Source dataset
uspto-grants-2013_04
Patent number
US08431738B2

Reaction notes

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