Acetyl chloride → HCID 69078908, compound

HRID 1724719Notes

Reaction equation

HRID 1724719 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.C([Cl:9])(=O)C.[NH2:10][C@@H:11]([C:14](O)=[O:15])[CH2:12][OH:13]>>[ClH:9].[NH2:10][C@H:11]([CH2:14][OH:15])[C:12]([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)=[O:13]

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 71077D-SerineHCID 75644Cyclopropanemethanol

Product 1

HCID 69078908HCID 69078908, compound

Procedure

Cyclopropylcarbinol (15 ml) is cooled to 0° C. and acetyl chloride (1.37 ml) is added. After being subjected to agitation for 10 minutes at 0° C., D-serine (750 mg) is added and the solution is brought to reflux for 2 hours. The reaction mixture is concentrated, recovered with a potassium carbonate saturated solution and extracted with ethyl acetate. The organic phase is dried on MgSO4, filtered and concentrated. The product is recovered in a minimum of methanol and a hydrochloric acid solution 1N is added in ether. The solvent is vacuum evaporated to obtain the desired product as a brown solid (250 mg). Melting point: 112-118° C.

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. customrecovered with a potassium carbonate saturated solution
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is recovered in a minimum of methanol
  9. additiona hydrochloric acid solution 1N is added in ether
  10. customevaporated

Sources & evidence

ORD record
ord-3d2ebb3f99e641eabc757741dbc7f3cf
Source dataset
uspto-grants-2009_02
Patent number
US07488755B2

Reaction notes

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