Acetyl chloride → L-Serine, ethyl ester, hydrochloride (1:1)

HRID 1815050Notes

Reaction equation

HRID 1815050 reaction equation
[NH2:1][C@@H:2]([CH2:6][OH:7])[C:3]([O-:5])=[O:4].[C:8]([Cl:11])(=O)[CH3:9]>C(O)C>[ClH:11].[NH2:1][C@@H:2]([CH2:6][OH:7])[C:3]([O:5][CH2:8][CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 5460791(2S)-2-amino-3-hydroxypropanoate

Product 1

HCID 2724185L-Serine, ethyl ester, hydrochloride (1:1)Yield 65.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2S)-2-amino-3-hydroxypropanoate (25 g, 238 mmol) and acetyl chloride (34 ml, 476 mmol) in absolute ethanol (250 ml) was stirred at 50° for 18 hr. The volatiles were removed in vacuo until the volume was reduced to ˜100 ml. Upon cooling the resultant precipitate was collected, washed with ether and hexane to give the title compound as a white powder (26.3 g, 65%). δH NMR (DMSO d6) 8.47 (3H, br s), 5.58 (1H, dd), 4.20 (2H, q), 4.08 (1H, t), 3.81 (2H, dd), 1.23 (3H, t).

Workup

  1. customThe volatiles were removed in vacuo until the volume
  2. temperatureUpon cooling the resultant precipitate
  3. customwas collected
  4. washwashed with ether and hexane

Sources & evidence

ORD record
ord-2361d80f27a54f8bb4eb5d4198ce7146
Source dataset
uspto-grants-2005_04
Patent number
US06878718B2

Reaction notes

Loading…