L-Serine → L-Serine, methyl ester, hydrochloride (1:1)

HRID 58835

Reaction equation

HRID 58835 reaction equation
[C:1]([Cl:4])(=O)C.[NH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][OH:8]>CO>[ClH:4].[NH2:5][C@@H:6]([CH2:7][OH:8])[C:9]([O:11][CH3:1])=[O:10]

Participants

4

Procedure

Methanol (450 mL) in a round-bottom flask was cooled to 0° C. and acetyl chloride (55 mL, 0.77 mol) was added dropwise. After completion of the addition, the mixture was stirred at ambient temperature for 10 min and H-Ser-OH (30 g, 0.29 mol) was added in three portions. The reaction mixture was heated at 80° C. for 2 h and then concentrated. The residue was dried under vacuum to afford (S)-methyl 2-amino-3-hydroxypropanoate hydrochloride (quantitative) as a colorless solid, which was used in the next step without further purification.

Workup

  1. additionAfter completion of the addition
  2. temperatureThe reaction mixture was heated at 80° C. for 2 h
  3. concentrationconcentrated
  4. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-0aa4fe0dd32d40968fc32e8b983d26a1
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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