Acetyl chloride → D-Serine methyl ester hydrochloride

HRID 62572

Reaction equation

HRID 62572 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[C:8]([Cl:11])(=O)C>CO>[ClH:11].[CH3:8][O:6][C:5](=[O:7])[C@@H:2]([CH2:3][OH:4])[NH2:1]

Participants

4

Procedure

D-serine (100 g, 0.9515 mole) was suspended in 600 ml methanol at room temperature. Acetyl chloride (224.0 g, 2.8545 mole) was added drop wise at −5° C. to 0° C. and stirred for 30 minutes. The reaction mixture was refluxed for 15 hours. Evaporation of the reaction mixture under reduced pressure followed by crystallization of the resulting residue from methanol and methyl tert-butyl ether, resulted in colorless solid of D-serine methyl ester hydrochloride (134.7 g, Yield: 91%, HPLC: 99.6%)

Workup

  1. temperatureThe reaction mixture was refluxed for 15 hours
  2. customEvaporation of the reaction mixture under reduced pressure
  3. customfollowed by crystallization of the resulting residue from methanol and methyl tert-butyl ether

Sources & evidence

ORD record
ord-3c91b85feed141eba2da4cf9e8233326
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Linked notes

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