Acetyl chloride → HCID 86755135, compound

HRID 377467Notes

Reaction equation

HRID 377467 reaction equation
[OH:1][C@@H:2]([C@@H:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](N)=[O:4].[C:14]([Cl:17])(=[O:16])[CH3:15]>C(O)C>[ClH:17].[OH:1][C@@H:2]([C@@H:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:16][CH2:14][CH3:15])=[O:4]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11171329rel-(αR,βR)-β-Amino-α-hydroxybenzenepropanamide

Product 1

HCID 86755135HCID 86755135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10.0 g of (2S, 3S) 2-hydroxy-3-amino-3-phenylpropionamide in 100 ml of ethanol was slowly added 16 ml of acetyl chloride at 0° C. The reaction mixture was refluxed for 40 h then cooled to room temperature. The reaction mixture was filtered to remove the ammonium chloride salt. The filtrate was concentrated to about one third of its original volume and diluted with 150 ml of ether. The precipitated product was filtered and washed with 100 ml of ether to give 10.9 g of ethyl (2S, 3S) 2-hydroxy-3-amino-3-phenylpropionate hydrochloride salt as a white powder, m.p. 149-151° C.; [α]D25 -25.6° (EtOH, c 1.1).

Workup

  1. customat 0° C
  2. temperatureThe reaction mixture was refluxed for 40 h
  3. filtrationThe reaction mixture was filtered
  4. customto remove the ammonium chloride salt
  5. concentrationThe filtrate was concentrated to about one third of its original volume
  6. additiondiluted with 150 ml of ether
  7. filtrationThe precipitated product was filtered
  8. washwashed with 100 ml of ether

Sources & evidence

ORD record
ord-44598d87c1b346d89c82157435c6d556
Source dataset
uspto-grants-2000_02
Patent number
US06025516

Reaction notes

Loading…