Acetyl chloride → HCID 45082407, compound

HRID 62573Notes

Reaction equation

HRID 62573 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][OH:8])[NH2:6].C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>ClCCl>[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][OH:8])[NH:6][C:17](=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11446470D-Serine methyl ester hydrochloride

Product 1

HCID 45082407HCID 45082407, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

D-Serine methyl ester hydrochloride (100 g, 0.6430 mole) was suspended in 500 ml dichloromethane. To this was added triethylamine (136.6 g, 1.35 mole) at 0-5° C., followed by acetyl chloride (53.06 g, 0.6751 mole) drop wise at −10° C. The reaction mixture was stirred at −10° C. for 3 hours, filtered to remove salts and the filtrate was evaporated. The resulting residue was suspended in 400 ml ethyl acetate and stirred for one hour. Salts were filtered and the ethyl acetate layer was concentrated under reduced pressure to get N-acetyl D-serine methyl ester as an oil (93.22 g, Yield: 90%, HPLC: 98.7%),

Workup

  1. filtrationfiltered
  2. customto remove salts
  3. customthe filtrate was evaporated
  4. stirringstirred for one hour
  5. filtrationSalts were filtered
  6. concentrationthe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ddb273fd859244429737029322cc5be1
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Reaction notes

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