Acetyl chloride → N-Acetyl-L-serine methyl ester

HRID 235710

Reaction equation

HRID 235710 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]>C(Cl)(Cl)Cl>[C:17]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][OH:8])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 7010549N-Acetyl-L-serine methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of about 46.57 g of L-serine methyl ester hydrochloride in about 3 liters of chloroform was added about 84 ml of triethylamine. This mixture was stirred until solution was complete, then about 21 ml of acetyl chloride was added dropwise. The mixture was then stirred under argon for about 2 days and the chloroform removed under reduced pressure. The residue was suspended in ethanol, filtered through a sintered glass funnel and the ethanol removed, giving about 49 g of the desired title compound [α]D26 =+36°±1° (CHCl3, 1.039%).

Workup

  1. stirringThe mixture was then stirred under argon for about 2 days
  2. customthe chloroform removed under reduced pressure
  3. filtrationfiltered through a sintered glass funnel
  4. customthe ethanol removed

Sources & evidence

ORD record
ord-a2cbcbd39a6b4bd0989d6e6ebf5761a8
Source dataset
uspto-grants-1987_02
Patent number
US04640913

Linked notes

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