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

HRID 491557Notes

Reaction equation

HRID 491557 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 500 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-746acc01b9364c7992fa8633ffd81c4e
Source dataset
uspto-grants-2009_05
Patent number
US07531549B2

Reaction notes

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